Benzamidoxime derivatives, method for preparation thereof and fungicide for agricultural and horticultural use

ABSTRACT

The present invention relates to benzamidoxime derivatives represented by the formula  I!; ##STR1## wherein R 1  is unsubstituted or substituted C 1  -C 4  alkyl, unsubstituted or substituted C 2  -C 4  alkenyl or unsubstituted or substituted C 2  -C 4  alkynyl, R 2  is phenyl optionally having substituents or heterocycle optionally having substituents X 1 , X 2 , X 3  and X 4  are each independently hydrogen, halogen, C 1  -C 4  alkyl, C 1  -C 4  haloalkyl, C 1  -C 4  alkoxy, C 1  -C 4  haloalkoxy, C 1  -C 4  alkylthio or the like, and r 1  and r 2  are each independently hydrogen, C 1  -C 4  alkyl or the like, having excellent fungicidal activity and being useful as a fungicide for agricultural and horticultural use, and methods for preparation thereof.

This is a continuation of application Ser. No. 08/849,811 filed Aug. 14, 1997, which is a 371 of PCT/JP95/02596, filed Dec. 18, 1995, now U.S. Pat. No. 5,847,005.

TECHNICAL FIELD

The present invention relates to novel benzamidoxime derivatives, methods for preparation thereof and fungicides for agricultural and horticultural uses.

BACKGROUND ART

In farming of agricultural and horticultural crops in the past, various fungicides have been used for the control of plant diseases on the crops, however, many of them are not enough useful because of their insufficient effectiveness in plant disease control, the limitation in their use due to the appearance of resistant strain of plant disease pathogens to the fungicides, the development of phytotoxicity and contamination to the crops, and/or their strong toxicity to humans, domestic animals and wildlife. For this reason, there is still intensive requirement to develop safe fungicides for agricultural and horticultural uses, which do not have the disadvantages as described above.

Some benzamidoxime derivatives, which are close to the compounds of the present invention, and their use as fungicides have been disclosed in Japanese Patent Laid-opened No. Hei 2-6453 Gazette. However, it is obvious that the biological activity of those benzamide oxime derivatives are not enough in the practical plant disease control.

Therefore, it is an object of the present invention to provide novel compounds which can be a fungicide for agricultural and horticultural use capable of advantageously manufacturing the compound in an industrial scale, controlling plant diseases steadily and using it safely.

DISCLOSURE OF THE INVENTION

The present invention is directed to benzamidoxime derivatives represented by a general formula I!; ##STR2## wherein R₁ is unsubstituted or substituted C₁ -C₄ alkyl, unsubstituted or substituted C₂ -C₄ alkenyl or unsubstituted or substituted C₂ -C₄ alkynyl, R² is phenyl optionally having substituents or heterocycle optionally having substituents, X¹ is C₁ -C₄ haloalkyl, X², X³, X⁴ and X⁵ are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl, nitro, amino or C₁ -C₄ alkylcarbonylamino, and r¹ and r² are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio or amino, or r¹ and r² may form carbonyl in together, and, the present invention is also directed to methods for preparation thereof and fungicides for agricultural and horticultural use comprising the said derivatives.

In the present invention, for the examples of C₁ -C₄ alkyl of the unsubstituted or substituted C₁ -C₄ alkyl represented by R¹, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and t-butyl can be given.

For the examples of C₂ -C₄ alkenyl of the unsubstituted or substituted C₂ -C₄ alkenyl represented by R¹, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl and 3-butenyl can be given.

For the examples of C₂ -C₄ alkynyl of the unsubstituted or substituted C₂ -C₄ alkynyl represented by R¹, ethynyl, propargyl, 2-butynyl and 3-butynyl can be given.

Further, in all of the unsubstituted or substituted C₁ -C₄ alkyl, the unsubstituted or substituted C₂ -C₄ alkenyl and the unsubstituted or substituted C₂ -C₄ alkynyl represented by R¹ ; C₃ -C₈ cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; C₃ -C₈ halocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2-fluorocyclopentyl, 3-flourocyclopentyl, 2-chlorocyclopentyl, 3-chlorocyclopentyl, 3,4-difluorocyclohexyl, 3,4-dichlorocyclohexyl and 3,4-dibromosilocyclohexy 1; C₃ -C₈ cycloalkenyl, such as 2-cyclohexenyl and 3-cyclohexenyl; halogens, such as fluorine, chlorine, bromine and iodine; C₁ -C₄ alkoxy, such as methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy and t-butyloxy; unsubstituted, mono-substituted or di-substituted amino by C₁ -C₄ alkyl, such as amino, methylamino and dimethylamino; unsubstituted, mono-substituted or di-substituted carbamoyl by C₁ -C₄ alkyl, such as carbamoyl, methylcarbamoyl and dimethylcarbamoyl; C₁ -C₄ alkylthio, such as methylthio, ethylthio, propylthio and isopropylthio; C₁ -C₄ alkylsulfinyl, such as methylsulfinyl and ethylsulfinyl; C₁ -C₄ alkylsulfonyl, such as methylsulfonyl and ethylsulfonyl; C₁ -C₄ alkoxycarbonyl, such as methoxycarbonyl and ethoxycarbonyl; carboxy and cyano, can be given for the examples of the substituents for any of C₁ -C₄ alkyl, C₂ -C₄ alkenyl and C₂ -C₄ alkynyl.

However, straight chain or branched C₁ -C₄ alkyl being unsubstituted or substituted is more preferable for the examples of the substituent represented by R¹. More particularly, straight chain or branched C₁ -C₄ alkyl, such as methyl, ethyl, propyl, isopropyl, butyl. s-butyl and t-butyl; a group represented by a general formula, R³ CH₂, wherein R³ is C₃ -C₈ cycloalkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl, C₁ -C₃ alkylsulfonyl, C₁ -C₃ alkoxycarbonyl, cyano, amino, C₁ -C₃ monoalkylamino, C₁ -C₃ dialkylamino or acylamino, such as C₁ -C₈ cycloalkylmethyl including cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl, C₁ -C₈ cyclohaloalkylmethyl including 2-fluorocyclopropylmethyl, 1-fluorocyclopropylmethyl, 1,2-difluorocyclopropylmethyl 3,4-dibromocyclohexyl, C₁ -C₄ haloalkyl including 2-chloroethyl, 2-fluoroethyl, 2,2-dichloroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl, C₁ -C₄ alkoxymethyl including methoxymethyl, ethoxymethyl and propoxymethyl, C₂ -C₄ alkynyl including propargyl, C₂ -C₄ alkenyl including allyl, 2-butenyl, cyanomethyl, alkoxycarbonylmethyl including methoxycarbonylmethyl and ethoxycarbonylmethyl, alkylthiomethyl including methylthiomethyl and ethylthiomethyl, alkylsulfinylmethyl including methylsulfinylmethyl and ethylsulfinylmethyl, alkylsulfonylmethyl including methylsulfonylmethyl and ethylsulfonylmethyl,aminomethyl, substituted aminomethyl including N-methylaminomethyl, N,N-dimethylaminomethyl, N-acetylaminomethyl and N-benzoylaminomethyl, can be given for the examples of the straight chain or branched C₁ -C₄ alkyl being unsubstituted or unsubstituted described above.

For the examples of heterocycle of the unsubstituted or substituted heterocycle group represented by R², 5- or 6-membered aromatic heterocycle containing 1-4 heteroatoms, such as N, O and S, such as pyridine ring, fran ring, thiophene ring, pyrazole ring, imidazole ring, triazole ring, pyrrole ring, pyrazine ring, pyrimidine ring, pyridazine ring, oxazole ring, isoxazole ring and thiazole ring, can be given.

The substituents for phenyl and heterocycle represented by R² may substitute one or more optional positions of the benzene ring or the heterocycle thereof and may be different with each other if 2 or more positions are substituted thereby. For the preferable examples of the substituents described hereinabove, halogens, such as fluorine, chlorine and bromine, C₁ -C₄ alkyl, such as methyl, ethyl, propyl, isopropyl, butyl and t-butyl, C₁ -C₄ alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy and t-butoxy, C₂ -C₄ alkenyloxy, such as allyoxy and crotyloxy, C₂ -C₄ alkynyloxy, such as propargyloxy, C₁ -C₄ haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trifluoroethoxy and pentafluoroethoxy, and C₁ -C₄ haloalkoxy, such as chloromethoxy, fluoromethoxy, bromomethoxy, dichloromethoxy, difluoromethoxy, trichloromethoxy, trifluoromethoxy, tribromomethoxy and trifluoroethoxy, can be given.

For the examples of the C₁ -C₄ haloalkyl represented by X¹, straight chain or branched C₁ -C₄ haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, bromomethyl, dibromomethyl, chloroethyl, fluoroethyl, dichloroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, chloropropyl, fluoropropyl, perfluoropropyl, chloroisopropyl, fluoroisopropyl, perfluoroisopropyl, chlorobutyl, fluorobutyl, perfluorobutyl, chloroisobutyl, fluoroisobutyl, perfluoroisobutyl, chloro-s-butyl, fluoro-s-butyl, perfluoro-s-butyl, chloro-t-butyl, fluoro-t-butyl and perfluoro-t-butyl, can be given.

For the examples of halogen atoms represented by X², X³, X⁴ and X⁵, fluorine, chlorine, bromine and iodine can be given, and for the examples of the C₁ -C₄ alkyl represented by X², X³, X⁴ and X⁵, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and t-butyl can be given, and further for the examples of the C₁ -C₄ haloalkyl represented by X², X³, X⁴ and X⁵, straight chain or branched C₁ -C₄ haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, bromomethyl, dibromomethyl, chloroethyl, fluoroethyl, dichloroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, chloropropyl, fluoropropyl, perfluoropropyl, chloroisopropyl, fluoroisopropyl, perfluoroisopropyl, chlorobutyl, fluorobutyl, perfluorobutyl, chloroisobutyl, fluoroisobutyl, perfluoroisobutyl, chloro-s-butyl, fluoro-s-butyl, perfluoro-s-butyl, chloro-t-butyl, fluoro-t-butyl and perfluoro-t-butyl, can be given, and still for the examples of the C₁ -C₄ alkoxy represented by X², X³, X⁴ and X⁵, methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy and t-butyloxy can be given. In addition, for the examples of the C₁ -C₄ alkylthio represented by X², X². X³, X⁴ and X⁵, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio and t-butylthio can be given, and for the examples of the C₁ -C₄ haloalkoxy represented by X², X³, X⁴ and X⁵, trifluoromethoxy, difluoromethoxy, trichloromethoxy, trifluoroethoxy and tetrafluoroethoxy can be given.

Furthermore, for the examples of the groups represented by r¹ and r², which may be the same or different groups with each other, hydrogen, halogen atoms, such as fluorine, chlorine, bromine and iodine, C₁ -C₄ alkyl, such as methyl, ethyl, propyl, isopropyl, butyl and t-butyl, C₁ -C₄ alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy and t-butoxy, C₁ -C₄ alkylthio, such as methylthio, ethylthio, propylthio, ispropylthio, butylthio and t-butylthio, C₁ -C₄ haloalkyl, such as trifluoromethyl, trichloromethyl, tribromomethyl, trifluoroethyl, chloromethyl, fluoromethyl and pentafluoroethyl, and amino can be given.

Moreover r¹ and r² may in together form a carbonyl group.

(Manufacturing of the Compounds)

The compounds of the present invention can be manufactured according to the following reaction formula; ##STR3## wherein Hal represents halogen, and R¹, R², X¹, X², X³, X⁴, X⁵, r₁ and r₂ are as described above.

The reaction described above is carried out by reacting the compound represented by the general formula II! and the compound represented by the general formula III! in an organic solvent for from 10 min. to several dozens of hours at a temperature range of from 0° C. to the boiling point of the solvent used and in the presence of a base, if appropriate.

For the examples of the solvent usable in the reaction described above, aromatic hydrocarbons, such as benzene and toluene, ethers, such as THF and diethyl ether, halogenated hydrocarbons, such as chloroform and dichloro methane, amides, such as DMF, DMSO, acetonitrile and the mixture of the solvent exemplified above, can be given.

As the base usable in the reaction, pyridine, triethyl amine, DBU, sodium hydroxide, sodium carbonate, potassium carbonate or the like can be exemplified.

After completed the reaction, the objective compounds can be obtained by taking an ordinary post-treatment procedure and allowing the products to the purification by using silica gel column chromatography or the else.

Whereas, the raw material compound of the present invention, represented by the general formula II! can be synthesized according to the following reaction formula; ##STR4## wherein L is an eliminating group, such as paratoluenesulfonyloxy, methylsulfonyloxy and halogen atoms, and R¹, X¹, X², X³, X⁴ and X⁵ are as described above.

The first step reaction in the reaction formula shown above is to obtain a benzamide oxime compound represented by the general formula V!, wherein a nitrile compound represented by the general formula IV! and hydroxyl amine hydrochloride are allowed to a reaction for 10 min. to several dozens of hours in an inactive solvent and in the presence of a base at a temperature range of from 0° C. to the boiling point of the solvent used.

For the examples of the solvent usable in the reaction described above, alcohols, such as methanol, ethanol and propanol, ethers, such as THF and diethyl ether, amides, such as DMF, DMSO, water and the mixture of the solvent exemplified hereinabove, can be given.

Further, for the examples of the base usable in the reaction described above, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, triethyl amine. pyridine and the like can be given.

The second step reaction in the reaction formula shown above is to obtain the raw material compound represented by the general formula II!, wherein the compound represented by the general formula VI! and a compound represented by a general formula, R¹ --L, are allowed to a reaction for 10 min. to several dozens of hours in a solvent and in the presence of a base at a temperature range of from -15° C. to the boiling point of the solvent used.

For the examples of the base usable in the second step reaction, metal alkoxide, such as sodium methoxide and sodium ethoxide, inorganic bases, such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, and organic bases, such as triethyl amine and pyridine, can be given.

Furthermore, if appropriate, catalysts may be used in the second step reaction, though it depends on the type of the solvent and the base to be used. For the examples of the catalysts usable in the reaction, crown ethers, such as 18-crown-6 and dicyclohexyl-18-crown-6, tetrabutyl ammonium bromide and other chlorides, quaternary ammonium salts, such as methyltrioctyl ammonium chloride and benzyltriethyl ammonium chloride, and phosphonium salts, such as tetraphenyl phosphonium bromide and hexadecyltributyl phosphonium iodide, can be given.

The chemical structures of the compounds of the present invention were determined by using NMR, IR, MS and the other analytical apparatuses.

BEST MODE FOR CARRYING OUT THE INVENTION

Now, the present invention is further described in detail with referring to the examples described hereinbelow.

EXAMPLE 1 Preparation of N'-cyclopropylmethyloxy-N-(4-methoxyphenyl)acetyl-2-fluoro-6-trifluoromethylbenzamidine (Compound No. 56) ##STR5##

In 200 ml of benzene was dissolved 20.0 g of N'-cyclopropylmethyloxy-2-fluoro-6-trifluoromethylbenzamidine, and to the solution was added 16. 0 g of 4-methoxyphenylacetylchloride. The solution was heated under refluxing for 10 hours. After cooling, ethyl acetate was added to the solution, followed by washing with water and drying over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain 23.6 g of the objective compound.m.p. 75-76° C.

EXAMPLE 2 Preparation N'-cyclopropylmethyloxy-N-(4-methoxyphenyl)acetyl-2-trifluoromethyl benzamidine (Compound No. 12) ##STR6##

In 80 ml of benzene was dissolved 10.4 g of N'-cyclopropylmethyloxy-2-fluoro-6-trifluoromethylbenzamidine, and to the solution was added 8.9 g of 4-methoxyphenylacetylchloride. The solution was heated under refluxing for 3 hours. After cooling, ethyl acetate was added to the solution, followed by washing with water and drying over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue obtained in crystal was washed with a mixed solvent hexane and ether to thereby obtain 13.7 g of crude crystal. The crystal was then re-crystallized in hexane, thereby affording 11.5 g of the objective compound.m.p. 88-90° C.

Now, the examples for preparing the raw material compounds described above to be used for the preparing of the compounds of the present invention are described hereinbelow.

Reference Example 1 Preparation of 2-fluoro-6-trifluoromethylbenzamidoxime ##STR7##

In 540 ml of methanol was dissolved 58.8 g of hydroxylamine hydrochloride and to the solution was added 160 ml of aqueous solution of sodium carbonate containing 49.4 g thereof. 40 g of 2-fluoro-6-trifluoromethylbenzonitrile was added thereto at room temperature with stirring, and then further stirred 3 hours at 60° C. After removing the solvent methanol by distillation from the solution, the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and it was concentrated under reduced pressure, thereby obtaining crude crystals. The crystals were then added with 200 ml of 3N aqueous solution of hydrochloric acid and thoroughly stirred, then the insoluble substance resulted in the solution was removed by filtration. The filtrate was then neutralized with 10% aqueous solution of sodium hydroxide under cooling and then extracted again with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solution was concentrated under reduced pressure to obtain 26.6 g of the objective compound. m.p. 155-157° C.

The examples of benzamide oxime derivatives represented by the general formula V!, which can be manufactured according to the methods as described above, are given in Table 1 hereinbelow.

                  TABLE 1                                                          ______________________________________                                         Chemical formula                                                               1 #STR8##                                                                      X.sup.2                                                                               X.sup.3   X.sup.4                                                                               X.sup.5 Physical const.                                ______________________________________                                         H      H         H      H       mp 124-126° C.                          H      H         H      Cl      mp 112-115° C.                          H      H         Cl     F       mp 107-108° C.                          H      H         Cl     Cl      n.sub.D.sup.24.0 1.5210                        H      H         H      F       mp 155-157° C.                          H      H         F      F       mp 105-107° C.                          H      H         F      Cl      mp 98-99° C.                            H      H         CF.sub.3                                                                              Cl      mp 97-99° C.                            ______________________________________                                    

Reference Example 2 Preparation of N'-cyclopropylmethyloxy-2-fluoro-6-trifluoromethylbenzamidine ##STR9##

In 100 ml of DMF was dissolved 26.6 g of 2-fluoro-6-trifluoromethylbenzamidoxime and 17.8 g of cyclopropylmethylbromide, and to the solution was added 4.8 g of sodium hydride (60% in oil) at 10° C. over 30 min. The solution was then stirred for 3 hours, and the solution reacted was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain 24.8 g of the objective compound. m.p. 63-64° C.

Reference Examples 3 Preparation of N'-cyclopropylmethyloxy-3,6-bistrifluoromethyl-2-chlorobenzamidine Preparation of N'-cyclopropylmethyloxy-3,6-bistrifluoromethyl-2-chlorobenzamidine ##STR10##

In 10 ml of chloroform was dissolved 0.60 g of 3,6-bistrifluoromethyl-2-chlorobenzamidoxime and 0. 50 g of cyclopropylmethylbromide, and to the solution was added 0.1 g of tetrabutylammonium bromide at room temperature with stirring, and then 1.2 ml of 10% aqueous solution of sodiumhydroxide, then stirred for 3 hours at 30-40° C. The solution was washed with water, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain 0.40 g of the objective compound.m.p. 75-80° C.

The examples of benzamidoxime derivatives represented by the general formula II!, which can be prepared according to the methods similar to the methods as described above, are given in Table 2 hereinbelow.

                  TABLE 2                                                          ______________________________________                                         Chemical formula                                                               2 #STR11##                                                                     X.sup.2                                                                              X.sup.3                                                                              X.sup.4  X.sup.5                                                                            R.sup.1    Physical const.                            ______________________________________                                         H     H     H        H   CH.sub.2 cPr                                                                              n.sub.D.sup.24.5 1.4917                    H     H     H        F   Et         mp 64-66° C.                        H     H     H        F   iPr        n.sub.D.sup.24.0 1.4789                    H     H     H        F   CH.sub.2 C(CH.sub.3).sub.3                                                                mp 97-98° C.                        H     H     H        F   CH.sub.2 CH═CH.sub.2                                                                  mp 69-70° C.                        H     H     H        F   CH.sub.2 C.tbd.CH                                                                         n.sub.D.sup.23.5 1.5011                    H     H     H        Cl  CH.sub.2 cPr                                                                              mp 43-46° C.                        H     H     Cl       F   CH.sub.2 cPr                                                                              mp 71-73° C.                        H     H     Cl       Cl  CH.sub.2 C.tbd.CH                                                                         n.sub.D.sup.23.5 1.5360                    Cl    H     H        Cl  CH.sub.2 cPr                                                                              n.sub.D.sup.23.5 1.5308                    H     H     Cl       Cl  CH.sub.2 cPr                                                                              mp 73-75° C.                        H     H     F        F   CH.sub.2 cPr                                                                              mp 43-45° C.                        H     H     F        Cl  CH.sub.2 cPr                                                                              mp 54-55° C.                        H     H     CF.sub.3 Cl  CH.sub.2 cPr                                                                              mp 75-78° C.                        ______________________________________                                          *cPr represents cyclopropylmethyl in the tables.                         

Now, the representative examples for the compounds of the present invention, which can be manufactured according to the preparation methods similar to the ones described in Examples 1 and 2, are given in Tables 3 and 4. However, it should be noted that X¹, X², X³, X⁴, X⁵, R¹, R², r₁ given in the Tables 3 and 4 correspond to X¹, X², X³, X⁴, X⁵, R¹, R², r₁ and r₂ given for the compounds represented by the general formula I!, respectively.

                                      TABLE 3                                      __________________________________________________________________________     (r.sup.1, r.sup.2 = H)                                                                                               Physical const.                                                                mp. (° C.)                        No.                                                                               X.sup.1                                                                           X.sup.2                                                                           X.sup.3                                                                          X.sup.4                                                                            X.sup.5                                                                            R.sup.1  R.sup.2   refractive index                         __________________________________________________________________________     1  CF.sub.3                                                                          H  H H   H   Et       Ph-4-OMe  72-73                                    2  CF.sub.3                                                                          H  H H   H   Me       Ph-4-OMe                                           3  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            2-thienyl 93-95                                    4  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            3-thienyl 92-93                                    5  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                                                           100-101                                  6  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-2-F    84-85                                    7  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-2-F, 4-OMe                                                                            84-85                                    8  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-3-Me   81-82                                    9  CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                                                            77-79                                    10 CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-4-F    113-114                                  11 CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-4-Me   80-81                                    12 CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph-4-OMe  88-90                                    13 CF.sub.3                                                                          H  H H   H   CH.sub.2 cPr                                                                            Ph        100-102                                  14 CF.sub.3                                                                          H  H H   H   nBu      Ph-4-OMe                                           15 CF.sub.3                                                                          H  H H   H   tBu      Ph-4-OMe                                           16 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe  n.sub.D.sup.27.0 1.5290                  17 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CH.sub.2                                                                Ph        n.sub.D.sup.28.5 1.5132                  18 CF.sub.3                                                                          H  H H   F   CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe  76-78                                    19 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CHCl                                                                    Ph-4-OMe  n.sub.D.sup.25.4 1.5333                  20 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CCl.sub.2                                                               Ph-4-OMe  n.sub.D.sup.25.7 1.5362                  21 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CH--CH.sub.3                                                            Ph-4-OMe  n.sub.D.sup.23.2 1.5148                  22 CF.sub.3                                                                          H  H H   F   Et       Ph-4-OMe  70-73                                    23 CF.sub.3                                                                          H  H H   F   Et       Ph        59-61                                    24 CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe  n.sub.D.sup.24.0 1.5330                  25 CF.sub.3                                                                          H  H H   F   CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe  78-80                                    26 CF.sub.3                                                                          H  H H   F   Me       Ph-4-OMe                                           27 CF.sub.3                                                                          H  H H   F   CH.sub.2 C(Cl)═CH.sub.2                                                             Ph-4-OMe  n.sub.D.sup.25.5 1.5242                  28 CF.sub.3                                                                          H  H H   F   CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe  n.sub.D.sup.25.0 1.5162                  29 CF.sub.3                                                                          H  H H   F   CH.sub.2 CN                                                                             Ph-4-OMe  n.sub.D.sup.23.5 1.5113                  30 CF.sub.3                                                                          H  H H   F   CH.sub.2 CN                                                                             Ph        n.sub.D.sup.23.5 1.5226                  31 CF.sub.3                                                                          H  H H   F   CH.sub.2 OCH.sub.3                                                                      Ph-4-OMe  n.sub.D.sup.24.0 1.5288                  32 CF.sub.3                                                                          H  H H   F   CH.sub.2 OCH.sub.3                                                                      Ph        n.sub.D.sup.24.5 1.5279                  33 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            3-methyl- n.sub.D.sup.21.8 1.5133                                              pyrazol-1-yl                                       34 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            4-methyl- n.sub.D.sup.23.8 1.5121                                              pyrazol-1-yl                                       35 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            pyrazol-1-yl                                                                             n.sub.D.sup.22.9 1.5126                  36 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            3-methyl- n.sub.D.sup.23.2 1.5310                                              2-thienyl                                          37 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            4-methyl- n.sub.D.sup.23.2 1.5313                                              2-thienyl                                          38 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            5-methyl- n.sub.D.sup.23.9 1.5353                                              2-thienyl                                          39 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            2-thienyl n.sub.D.sup.22.2 1.5346                  40 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            4-methyl- n.sub.D.sup.28.5 1.5302                                              3-thienyl                                          41 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            5-methyl- 57-58                                    42 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            3-thienyl 70-72                                    43 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                                                           n.sub.D.sup.26.0 1.5083                  44 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-F    n.sub.D.sup.26.0 1.5191                  45 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                                                              n.sub.D.sup.23.4 1.5197                  46 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                                                             n.sub.D.sup.27.5 1.5193                  47 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                            n.sub.D.sup.27.0 1.6190                                              5-Me                                               48 CF.sub.3                                                                          H  H H   F   CH.sub.2 CPr                                                                            Ph-2-F-5-Me                                                                              n.sub.D.sup.26.7 1.5153                  49 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3.5-Me.sub.2                                                                          88-89                                    50 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3-Et   63-64                                    51 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3-Me   52-53                                    52 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                                                              73-74                                    53 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                                                            n.sub.D.sup.26.0 1.5307                  54 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-F    58-59                                    55 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OMe  n.sub.D.sup.26.0 1.5248                  56 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OMe  75-76                                    57 CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph        72-74                                    58 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       2-thienyl 54-56                                    59 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       3-thienyl 56-58                                    60 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F    57-58                                    61 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F-4-OMe                                                                             n.sub.D.sup.22.5 1.5257                  62 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-Me                                                                              n.sub.D.sup.26.0 1.5192                  63 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-3,5-Me.sub.2                                                                          98-100                                   64 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-4-Me   95-96                                    65 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe  n.sub.D.sup.27.5 1.5370                  66 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CH                                                                       Ph        58-60                                    67 CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.Cl                                                                       Ph-4-OMe  n.sub.D.sup.22.5 1.5557                  68 CF.sub.3                                                                          H  H H   F   iPr      Ph-4-OMe  85-86                                    69 CF.sub.3                                                                          H  H H   F   iPr      Ph        84-85                                    70 CF.sub.3                                                                          H  H H   F   nBu      Ph                                                 71 CF.sub.3                                                                          H  H H   F   nPr      Ph-2-F-4-OMe                                                                             n.sub.D.sup.18.5 1.5121                  72 CF.sub.3                                                                          H  H H   F   nPr      Ph-2-F-5-Me                                                                              n.sub.D.sup.18.0 1.5129                  73 CF.sub.3                                                                          H  H H   F   nPr      Ph-4-Me   59-60                                    74 CF.sub.3                                                                          H  H H   F   nPr      Ph-4-OMe  54-55                                    75 CF.sub.3                                                                          H  H H   F   nPr      Ph        n.sub.D.sup.26.5 1.5106                  76 CF.sub.3                                                                          H  H H   F   tBu      Ph                                                 77 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           78 CF.sub.3                                                                          H  H H   Cl  CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe                                           79 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CH═CHCl                                                                    Ph-4-OMe                                           80 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CH═CCl.sub.2                                                               Ph-4-OMe                                           81 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CH═CHCH.sub.3                                                              Ph-4-OMe                                           82 CF.sub.3                                                                          H  H H   Cl  Et       Ph-4-OMe  68-70                                    83 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           84 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe                                           85 CF.sub.3                                                                          H  H H   Cl  Me       Ph-4-OMe                                           86 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 C(Cl)CH.sub.2                                                                  Ph-4-OMe                                           87 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe                                           88 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 CN                                                                             Ph-4-OMe                                           89 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 OMe                                                                            Ph-4-OMe                                           90 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       91 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       92 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            pyrazol-1-yl                                       93 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          94 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          95 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          96 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            2-thienyl 47-49                                    97 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          98 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          99 CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            3-thienyl 74-76                                    100                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     101                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F                                             102                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        103                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                       104                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               105                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                                                              n.sub.D.sup.23.8 1.5323                  106                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    107                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-3-Me                                            108                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                        109                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      110                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-4-F                                             111                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-4-Me                                            112                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe  65-67                                    113                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 cPr                                                                            Ph        63-65                                    114                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe  76-78                                    115                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 C.tbd.CH                                                                       Ph        96-97                                    116                                                                               CF.sub.3                                                                          H  H H   Cl  CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           117                                                                               CF.sub.3                                                                          H  H H   Cl  iPr      Ph-4-OMe                                           118                                                                               CF.sub.3                                                                          H  H H   Cl  nBu      Ph-4-OMe                                           119                                                                               CF.sub.3                                                                          H  H H   Cl  nPr      Ph-4-OMe                                           120                                                                               CF.sub.3                                                                          H  H H   Cl  tBu      Ph-4-OMe                                           121                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           122                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe                                           123                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CH═CHCl                                                                    Ph-4-OMe                                           124                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CH═CCl.sub.2                                                               Ph-4-OMe                                           125                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CH═CHCH.sub.3                                                              Ph-4-OMe                                           126                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           Et       Ph-4-OMe                                           127                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           128                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe                                           129                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           Me       Ph-4-OMe                                           130                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 C(Cl)═CH.sub.2                                                             Ph-4-OMe                                           131                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe                                           132                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 CN                                                                             Ph-4-OMe                                           133                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 OMe                                                                            Ph-4-OMe                                           134                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       135                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       136                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                                             pyrazol-1-yl                                       137                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          138                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          139                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          140                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            2-thienyl n.sub.D.sup.22.4 1.5082                  141                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          142                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          143                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            3-thienyl                                          144                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     145                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F                                             146                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        147                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                       148                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               149                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                                                              74-75                                    150                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    151                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-3-Me                                            152                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                        153                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      154                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-F                                             155                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-Me                                            156                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe  n.sub.D.sup.22.6 1.5031                  157                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph        68-69                                    158                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           159                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           160                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           iPr      Ph-4-OMe                                           161                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           nBu      Ph-4-OMe                                           162                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           nPr      Ph-4-OMe                                           163                                                                               CF.sub.3                                                                          H  H H   CF.sub.3                                                                           tBu      Ph-4-OMe                                           164                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           165                                                                               CF.sub.3                                                                          H  H H   OMe CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe                                           166                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CH═CHCl                                                                    Ph-4-OMe                                           167                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CH═CCl.sub.2                                                               PH-4-OMe                                           168                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CH═CHCH.sub.3                                                              Ph-4-OMe                                           169                                                                               CF.sub.3                                                                          H  H H   OMe Et       Ph-4-OMe  95-96                                    170                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           171                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe                                           172                                                                               CF.sub.3                                                                          H  H H   OMe Me       Ph-4-OMe                                           173                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 C(Cl)═CH.sub.2                                                             Ph-4-OMe                                           174                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe                                           175                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 CN                                                                             Ph-4-OMe                                           176                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 OMe                                                                            Ph-4-OMe                                           177                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       178                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       179                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            pyrazol-1-yl                                       180                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          181                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          182                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          183                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            2-thienyl                                          184                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          185                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          186                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            3-thienyl                                          187                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     188                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2-F                                             189                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        190                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                       191                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               192                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        193                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    194                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3-Me                                            195                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                        196                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      197                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-4-F                                             198                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-4-Me                                            199                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-4-OMe  92-93                                    200                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3-Cl-4-OMe                                      201                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph-3-Cl-4-OMe-                                                                 5-Me                                               202                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 cPr                                                                            Ph                                                 203                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           204                                                                               CF.sub.3                                                                          H  H H   OMe CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           205                                                                               CF.sub.3                                                                          H  H H   OMe iPr      Ph-4-OMe                                           206                                                                               CF.sub.3                                                                          H  H H   OMe nBu      Ph-4-OMe                                           207                                                                               CF.sub.3                                                                          H  H H   OMe nPr      Ph-4-OMe                                           208                                                                               CF.sub.3                                                                          H  H H   OMe tBu      Ph-4-OMe                                           209                                                                               CF.sub.3                                                                          H  H H   SMe Et       Ph-4-OMe  89-90                                    210                                                                               CF.sub.3                                                                          H  H H   SMe Me       Ph-4-OMe                                           211                                                                               CF.sub.3                                                                          H  H H   SMe CH.sub.2 cPr                                                                            Ph-4-OMe  73-75                                    212                                                                               CF.sub.3                                                                          H  H H   SMe CH.sub.2 cPr                                                                            Ph        106-109                                  213                                                                               CF.sub.3                                                                          H  H H   SMe nBu      Ph-4-OMe                                           214                                                                               CF.sub.3                                                                          H  H H   SMe tBu      Ph-4-OMe                                           215                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           216                                                                               CF.sub.3                                                                          H  H Cl  H   Et       Ph-4-OMe                                           217                                                                               CF.sub.3                                                                          H  H Cl  H   Me       Ph-4-OMe                                           218                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            3-methyl-                                                                      pyraozol-1-yl                                      219                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       220                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            pyrazol-1-yl                                       221                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          222                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          223                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          224                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            2-thienyl                                          225                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          226                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          227                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            3-thienyl                                          228                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 cPr                                                                            Ph-4-OMe                                           229                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           230                                                                               CF.sub.3                                                                          H  H Cl  H   iPr      Ph-4-OMe                                           231                                                                               CF.sub.3                                                                          H  H Cl  H   nBu      Ph-4-OMe                                           232                                                                               CF.sub.3                                                                          H  H Cl  H   nPr      Ph-4-OMe                                           233                                                                               CF.sub.3                                                                          H  H Cl  H   tBu      Ph-4-OMe                                           234                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe  81-83                                    235                                                                               CF.sub.3                                                                          H  H Cl  F   CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe                                           236                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CHCl                                                                    Ph-4-OMe                                           237                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CCl.sub.2                                                               Ph-4-OMe                                           238                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CHCH.sub.3                                                              Ph-4-OMe                                           239                                                                               CF.sub.3                                                                          H  H Cl  F   Et       Ph-4-OMe   99-100                                  240                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe  n.sub.D.sup.24 1.5301                    241                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph        90-91                                    242                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-4-Me                                                                              n.sub.D.sup.24.0 1.5241                  243                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe                                           244                                                                               CF.sub.3                                                                          H  H Cl  F   Me       Ph-4-OMe                                           245                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C(Cl)═CH.sub.2                                                             Ph-4-OMe                                           246                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe                                           247                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CN                                                                             Ph-4-OMe                                           248                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 OMe                                                                            Ph-4-OMe                                           249                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       250                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       251                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            pyrazol-1-yl                                       252                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          253                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          254                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          255                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            2-thienyl 112-113                                  256                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          257                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          258                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            3-thienyl 125-126                                  259                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     260                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F    57-59                                    261                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        262                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2F-4-OMe                                                                              n.sub.D.sup.26.7 1.5200                  263                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                            73-74                                                                5-Me                                               264                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                                                              60-62                                    265                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    266                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-3-Me   92-93                                    267                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                                                              98-99                                    268                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                                                            86-87                                    269                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-4-F    94-95                                    270                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-4-Me   75-76                                    271                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph-4OMe    98                                      272                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 cPr                                                                            Ph        112                                      273                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CH                                                                       Ph        54-58                                    274                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-Me                                                                              91-92                                    275                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe  102-103                                  276                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe  112-114                                  277                                                                               CF.sub.3                                                                          H  H Cl  F   iPr      Ph-4-OMe  124-125                                  278                                                                               CF.sub.3                                                                          H  H Cl  F   nBu      Ph-4-OMe                                           279                                                                               CF.sub.3                                                                          H  H Cl  F   nPr      Ph-4-OMe  90-91                                    280                                                                               CF.sub.3                                                                          H  H Cl  F   tBu      Ph-4-OMe                                           281                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe  80-81                                    282                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH(CH.sub.3)CH═CH.sub.2                                                             Ph-4-OMe                                           283                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CHCl                                                                    Ph-4-OMe                                           284                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CCl.sub.2                                                               Ph-4-OMe                                           285                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CHCH.sub.3                                                              Ph-4-OMe                                           286                                                                               CF.sub.3                                                                          H  H Cl  Cl  Et       Ph        123-124                                  287                                                                               CF.sub.3                                                                          H  H Cl  Cl  Et       Ph-2-F-5-Me                                                                              78-81                                    288                                                                               CF.sub.3                                                                          H  H Cl  Cl  Et       Ph-4-OMe  90-91                                    289                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph        104-105                                  290                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-5-OMe                                                                             n.sub.D.sup.28.5 1.5309                  291                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           292                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CHF.sub.2                                                                      Ph-4-OMe                                           293                                                                               CF.sub.3                                                                          H  H Cl  Cl  Me       Ph-4-OMe  77-79                                    294                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C(Cl)═CH.sub.2                                                             Ph-4-OMe                                           295                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C(CH.sub.3)═CH.sub.2                                                       Ph-4-OMe                                           296                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CN                                                                             Ph-4-OMe                                           297                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 OMe                                                                            Ph-4-OMe                                           298                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       299                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       300                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            pyrazol-1-yl                                       301                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          302                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          303                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          304                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            2-thienyl 139-141                                  305                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          306                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          307                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            3-thienyl 140-141                                  308                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     309                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F    n.sub.D.sup.23.0 1.5404                  310                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        311                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                                                             n.sub.D.sup.22.5 1.5371                  312                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2F-4-OMe-                                                                             n.sub.D.sup.23.5 1.5287                                              5-Me                                               313                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                                                              56-57                                    314                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    315                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-3-Me   111-114                                  316                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                                                              113-114                                  317                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      318                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-F                                             319                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-Me   93-95                                    320                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe  97-98                                    321                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph        134-135                                  322                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph        96-98                                    323                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-Me                                                                              77-79                                    324                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe  94-96                                    325                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           326                                                                               CF.sub.3                                                                          H  H Cl  Cl  iPr      Ph-4-OMe  123-124                                  327                                                                               CF.sub.3                                                                          H  H Cl  Cl  nBu      Ph-4-OMe                                           328                                                                               CF.sub.3                                                                          H  H Cl  Cl  nPr      Ph-4-OMe  88-89                                    329                                                                               CF.sub.3                                                                          H  H Cl  Cl  tBu      Ph-4-OMe                                           330                                                                               CF.sub.3                                                                          H  H SMe F   CH.sub.2 cPr                                                                            Ph-4-OMe  114-115                                  331                                                                               CF.sub.3                                                                          H  H OMe F   CH.sub.2 cPr                                                                            Ph-4-OMe  125-126                                  332                                                                               CF.sub.3                                                                          H  H OMe F   CH.sub.2 cPr                                                                            Ph-4-OMe  135-136                                  333                                                                               CF.sub.3                                                                          H  H Me  F   CH.sub.2 cPr                                                                            Ph-4-OMe  71-72                                    334                                                                               CF.sub.3                                                                          H  F H   H   Et       Ph-4-OMe  70-72                                    335                                                                               CF.sub.3                                                                          H  F H   H   Me       Ph-4-OMe                                           336                                                                               CF.sub.3                                                                          H  F H   H   CH.sub.2 cPr                                                                            Ph-4-OMe  97-99                                    337                                                                               CF.sub.3                                                                          H  F H   H   CH.sub.2 cPr                                                                            Ph        117-119                                  338                                                                               CF.sub.3                                                                          H  F H   H   nBu      Ph-4-OMe                                           339                                                                               CF.sub.3                                                                          H  F H   H   tBu      Ph                                                 340                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   Et       Ph-4-OMe  89-91                                    341                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   Me       Ph-4-OMe                                           342                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   CH.sub.2 cPr                                                                            Ph-4-OMe  97-99                                    343                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   CH.sub.2 cPr                                                                            Ph        91-92                                    344                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   nBu      Ph-4-OMe                                           345                                                                               CF.sub.3                                                                          H  Cl                                                                               H   H   tBu      Ph                                                 346                                                                               CF.sub.3                                                                          Cl H H   F   CH.sub.2 cPr                                                                            Ph-4-OMe  Oil, *1                                  347                                                                               CF.sub.3                                                                          Cl H H   Cl  CH.sub.2 cPr                                                                            2-thienyl  74                                      348                                                                               CF.sub.3                                                                          Cl H H   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe  100                                      349                                                                               CF.sub.3                                                                          Cl H H   Cl  CH.sub.2 cPr                                                                            Ph        95-96                                    350                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           351                                                                               CF.sub.3                                                                          H  H F   F   Et       Ph        81-83                                    352                                                                               CF.sub.3                                                                          H  H F   F   Et       Ph-2-F-5-Me                                                                              79-80                                    353                                                                               CF.sub.3                                                                          H  H F   F   Et       Ph-4-OMe  78-79                                    354                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph        n.sub.D.sup.23.5 1.5245                  355                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-5-Me                                        356                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           357                                                                               CF.sub.3                                                                          H  H F   F   Me       Ph-4-OMe                                           358                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 OMe                                                                            Ph-4-OMe                                           359                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       360                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       361                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            pyrazol-1-yl                                       362                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          363                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          364                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2-F    56-58                                    365                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        366                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2F-4-OMe                                        367                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2F-4-OMe-                                                                             70-73                                                                5-Me                                               368                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2F-5-Me                                                                               67-69                                    369                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    370                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-3-Me   70-72                                    371                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                                                              51-53                                    372                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                                                            56-57                                    373                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-F    70-72                                    374                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-Me   64-66                                    375                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OMe  73-74                                    376                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph        61-62                                    377                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph        76-78                                    378                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-OMe                                                                             84-86                                    379                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe  100-102                                  380                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           381                                                                               CF.sub.3                                                                          H  H F   F   iPr      Ph-4-OMe  65-66                                    382                                                                               CF.sub.3                                                                          H  H F   F   nBu      Ph-4-OMe                                           383                                                                               CF.sub.3                                                                          H  H F   F   nPr      Ph-4-OMe  67-69                                    384                                                                               CF.sub.3                                                                          H  H F   F   tBu      Ph-4-OMe                                           385                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          386                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-thienyl 69-71                                    387                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          388                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          389                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-thienyl 79-81                                    390                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     391                                                                               CF.sub.3                                                                          H  H Cl  F   nPr      Ph        113-114                                  392                                                                               CF.sub.3                                                                          H  H Cl  F   nPr      Ph-2-F-5-Me                                                                              60-61                                    393                                                                               CF.sub.3                                                                          H  H Cl  F   iPr      Ph        111-112                                  394                                                                               CF.sub.3                                                                          H  H Cl  F   iPr      Ph-2-F-5-Me                                        395                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CH.sub.2                                                                Ph        107-108                                  396                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                                                              68-70                                    397                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.3 Ph                                                 398                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.3 Ph-2-F-5-Me                                        399                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CI                                                                       Ph        90-91                                    400                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 C.tbd.CI                                                                       Ph-2-F-5-Me                                                                              n.sub.D.sup.25.0 1.5491                  401                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH.sub.3                                                                       Ph        101-102                                  402                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 CH.sub.3                                                                       Ph-2-F-5-Me                                                                              60-62                                    403                                                                               CF.sub.3                                                                          H  H Cl  Cl  nPr      Ph        128-129                                  404                                                                               CF.sub.3                                                                          H  H Cl  Cl  nPr      Ph-2-F-5-Me                                                                              n.sub.D.sup.24.0 1.5212                  405                                                                               CF.sub.3                                                                          H  H Cl  Cl  iPr      Ph        125-127                                  406                                                                               CF.sub.3                                                                          H  H Cl  Cl  iPr      Ph-2-F-5-Me                                                                              n.sub.D.sup.24.7 1.5245                  407                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CH.sub.2                                                                Ph        115-116                                  408                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                                                              62-63                                    409                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.3 Ph        111-113                                  410                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.3 Ph-2-F-5-Me                                                                              80-81                                    411                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CI                                                                       Ph                                                 412                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 C.tbd.CI                                                                       Ph-2-F-5-Me                                        413                                                                               CF.sub.3                                                                          H  H F   F   nPr      Ph        56-58                                    414                                                                               CF.sub.3                                                                          H  H F   F   nPr      Ph-2-F-5-Me                                                                              38-40                                    415                                                                               CF.sub.3                                                                          H  H F   F   iPr      Ph          81-82.5                                416                                                                               CF.sub.3                                                                          H  H F   F   iPr      Ph-2-F-5-Me                                        417                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH═CH.sub.2                                                                Ph                                                 418                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                        419                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.3 Ph                                                 420                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.3 Ph-2-F-5-Me                                        421                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CI                                                                       Ph                                                 422                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CI                                                                       hH-2-F-5-Me                                        423                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH═CH.sub.2                                                                Ph                                                 424                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           425                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                        426                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 427                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           428                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph-2-F-5-Me                                        429                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph        n.sub.D.sup.24.5 1.5344                  430                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe  n.sub.D.sup.24.5 1.5294                  431                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-5-Me                                        432                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.3 Ph                                                 433                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.3 Ph-4-OMe                                           434                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.3 Ph-2-F-5-Me                                        435                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 OMe                                                                            Ph-4-OMe                                           436                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       437                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       438                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            pyrazol-1-yl                                       439                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          440                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          441                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          442                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            2-thienyl 104-106                                  443                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          444                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          445                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            3-thienyl 113-115                                  446                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     447                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F    n.sub.D.sup.23.8 1.5262                  448                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                       449                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-2-OMe                                       450                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               451                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                                                              62-63                                    452                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    453                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-3-Me   96-98                                    454                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                                                              82-83                                    455                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                                                            72-73                                    456                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-4-F    76-77                                    457                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-4-Me   75-76                                    458                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe  68-69                                    459                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 Pr                                                                             Ph        102-104                                  460                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 461                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           462                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-OMe                                       463                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           464                                                                               CF.sub.3                                                                          H  H F   Cl  iPr      Ph                                                 465                                                                               CF.sub.3                                                                          H  H F   Cl  iPr      Ph-4-OMe                                           466                                                                               CF.sub.3                                                                          H  H F   Cl  iPr      Ph-2-F-5-Me                                        467                                                                               CF.sub.3                                                                          H  H F   Cl  nPr      Ph                                                 468                                                                               CF.sub.3                                                                          H  H F   Cl  nPr      Ph-4-OMe                                           469                                                                               CF.sub.3                                                                          H  H F   Cl  nPr      Ph-2-F-5-Me                                        470                                                                               CF.sub.3                                                                          H  H F   Cl  nBu      Ph-4-OMe                                           471                                                                               CF.sub.3                                                                          H  H F   Cl  tBu      Ph-4-OMe                                           472                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH═CH.sub.2                                                                Ph                                                 473                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           474                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                        475                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 476                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           477                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.3                                                                       Ph-2-F-5-Me                                        478                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 479                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           480                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-5-Me                                        481                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.3 Ph                                                 482                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.3 Ph-4-OMe                                           483                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.3 Ph-2-F-5-Me                                        484                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 OMe                                                                            Ph-4-OMe                                           485                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      pyrazol-1-yl                                       486                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      pyrazol-1-yl                                       487                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            pyrazol-1-yl                                       488                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          489                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          490                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          491                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            2-thienyl                                          492                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          493                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          494                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            3-thienyl                                          495                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     496                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2-F                                             497                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        498                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OM                                        499                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               500                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        501                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-2,5-Me.sub.2                                    502                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-3-Me                                            503                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                        504                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      505                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-4-F                                             506                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-4-Me                                            507                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           508                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph        65-67                                    509                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 510                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           511                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-Me                                        512                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  CH.sub.2 C.tbd.CI                                                                       Ph                                                 513                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  iPr      Ph                                                 514                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  iPr      Ph-4-OMe                                           515                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  iPr      Ph-2-F-5-Me                                        516                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  nPr      Ph                                                 517                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  nPr      Ph-4-OMe                                           518                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  nPr      Ph-2-F-5-Me                                        519                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  nBu      Ph-4-OMe                                           520                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           Cl  tBu      Ph-4-OMe                                           521                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH═CH.sub.2                                                                Ph                                                 522                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH═CH.sub.2                                                                Ph-4-OMe                                           523                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH═CH.sub.2                                                                Ph-2-F-5-Me                                        524                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.3                                                                       Ph                                                 525                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           526                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.3                                                                       Ph-2-F-5-Me                                        527                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 528                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-4-OMe                                           529                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 CH.sub.2 Cl                                                                    Ph-2-F-5-Me                                        530                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.3 Ph                                                 531                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.3 Ph-4-OMe                                           532                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.3 Ph-2-F-5-Me                                        533                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 OMe                                                                            Ph-4-OMe                                           534                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            3-methyl-                                                                      2-thienyl                                          535                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            4-methyl-                                                                      2-thienyl                                          536                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            5-methyl-                                                                      2-thienyl                                          537                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            2-thienyl                                          538                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          539                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          540                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            3-thienyl                                          541                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            4-methyl-                                                                      3-thienyl                                          542                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            5-methyl-                                                                      3-thienyl                                          543                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            3-thienyl                                          544                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2,4-F.sub.2                                     545                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2-F                                             546                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2-F-3-Me                                        547                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2-F-4-OMe                                       548                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2-F-4-OMe-                                                                  5-Me                                               549                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        550                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-3,5-Me.sub.2                                    551                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-3-Me                                            552                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-3-Me-4-F                                        553                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-3-Me-4-OMe                                      554                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-4-F                                             555                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-4-Me                                            556                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           557                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph                                                 558                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 559                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 C.tbd.CH                                                                       Ph-4-OMe                                           560                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 C.tbd.CH                                                                       Ph-2-F-5-Me                                        561                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   CH.sub.2 C.tbd.CI                                                                       Ph-4-OMe                                           562                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   iPr      Ph                                                 563                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   iPr      Ph-4-OMe                                           564                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   iPr      Ph-2-F-5-Me                                        565                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   nPr      Ph                                                 566                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   nPr      Ph-4-OMe                                           567                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   nPr      Ph-2-F-5-Me                                        568                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   nBu      Ph-4-OMe                                           569                                                                               CF.sub.3                                                                          H  H CF.sub.3                                                                           F   tBu      Ph-4-OMe                                           570                                                                               CF.sub.3                                                                          F  H H   Cl  CH.sub. cPr                                                                             Ph                                                 571                                                                               CF.sub.3                                                                          F  H H   Cl  CH.sub. cPr                                                                             Ph-4-OMe                                           572                                                                               CF.sub.3                                                                          F  H H   Cl  CH.sub. cPr                                                                             Ph-2-F-5-Me                                        573                                                                               CF.sub.3                                                                          F  H H   F   CH.sub.2 cPr                                                                            Ph                                                 574                                                                               CF.sub.3                                                                          F  H H   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           575                                                                               CF.sub.3                                                                          F  H H   F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        576                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   Cl  CH.sub.2 cPr                                                                            Ph                                                 577                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           578                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        579                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   F   CH.sub.2 cPr                                                                            Ph                                                 580                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           581                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        582                                                                               CF.sub.3                                                                          Cl H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 583                                                                               CF.sub.3                                                                          Cl H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           584                                                                               CF.sub.3                                                                          Cl H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        585                                                                               CF.sub.3                                                                          F  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 586                                                                               CF.sub.3                                                                          F  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           587                                                                               CF.sub.3                                                                          F  H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        588                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 589                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           590                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H H   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        591                                                                               CF.sub.3                                                                          H  H H   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 592                                                                               CF.sub.3                                                                          H  H H   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           593                                                                               CF.sub.3                                                                          H  H H   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        594                                                                               CF.sub.3                                                                          H  H F   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 595                                                                               CF.sub.3                                                                          H  H F   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           596                                                                               CF.sub.3                                                                          H  H F   CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        597                                                                               CF.sub.3                                                                          H  H Cl  CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 598                                                                               CF.sub.3                                                                          H  H Cl  CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           599                                                                               CF.sub.3                                                                          H  H Cl  CH.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        600                                                                               CF.sub.3                                                                          F  H F   F   CH.sub.2 cPr                                                                            Ph                                                 601                                                                               CF.sub.3                                                                          F  H F   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           602                                                                               CF.sub.3                                                                          F  H F   F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        603                                                                               CF.sub.3                                                                          F  H F   Cl  CH.sub.2 cPr                                                                            Ph                                                 604                                                                               CF.sub.3                                                                          F  H F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           605                                                                               CF.sub.3                                                                          F  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        606                                                                               CF.sub.3                                                                          F  H Cl  F   CH.sub.2 cPr                                                                            Ph                                                 607                                                                               CF.sub.3                                                                          F  H Cl  F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           608                                                                               CF.sub.3                                                                          F  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        609                                                                               CF.sub.3                                                                          F  H Cl  Cl  CH.sub.2 cPr                                                                            Ph                                                 610                                                                               CF.sub.3                                                                          F  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           611                                                                               CF.sub.3                                                                          F  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        612                                                                               CF.sub.3                                                                          Cl H F   F   CH.sub.2 cPr                                                                            Ph                                                 613                                                                               CF.sub.3                                                                          Cl H F   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           614                                                                               CF.sub.3                                                                          Cl H F   F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        615                                                                               CF.sub.3                                                                          Cl H F   Cl  CH.sub.2 cPr                                                                            Ph                                                 616                                                                               CF.sub.3                                                                          Cl H F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           617                                                                               CF.sub.3                                                                          Cl H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        618                                                                               CF.sub.3                                                                          Cl H Cl  F   CH.sub.2 cPr                                                                            Ph                                                 619                                                                               CF.sub.3                                                                          Cl H Cl  F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           620                                                                               CF.sub.3                                                                          Cl H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        621                                                                               CF.sub.3                                                                          Cl H Cl  Cl  CH.sub.2 cPr                                                                            Ph                                                 622                                                                               CF.sub.3                                                                          Cl H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           623                                                                               CF.sub.3                                                                          Cl H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        624                                                                               CF.sub.3                                                                          Cl H Cl  CF.sub.3                                                                           CH.sub.2 CPr                                                                            Ph                                                 625                                                                               CF.sub.3                                                                          Cl H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 626                                                                               CF.sub.3                                                                          F  H Cl  CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 627                                                                               CF.sub.3                                                                          F  H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 628                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  Cl  CH.sub.2 cPr                                                                            Ph                                                 629                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  F   CH.sub.2 cPr                                                                            Ph                                                 630                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   Cl  CH.sub.2 cPr                                                                            Ph                                                 631                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   F   CH.sub.2 cPr                                                                            Ph                                                 632                                                                               CF.sub.3                                                                          Cl H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph                                                 633                                                                               CF.sub.3                                                                          F  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph                                                 634                                                                               CF.sub.3                                                                          Cl H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph                                                 635                                                                               CF.sub.3                                                                          F  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph                                                 636                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 637                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 638                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H CF.sub.3                                                                           CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph                                                 639                                                                               CF.sub.3                                                                          F  F F   F   CH.sub.2 cPr                                                                            Ph                                                 640                                                                               CF.sub.3                                                                          F  F F   Cl  CH.sub.2 cPr                                                                            Ph                                                 641                                                                               CF.sub.3                                                                          F  F Cl  F   CH.sub.2 cPr                                                                            Ph                                                 642                                                                               CF.sub.3                                                                          F  F Cl  Cl  CH.sub.2 cPr                                                                            Ph                                                 643                                                                               CF.sub.3                                                                          Cl H Cl  CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           644                                                                               CF.sub.3                                                                          Cl H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           645                                                                               CF.sub.3                                                                          F  H Cl  CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           646                                                                               CF.sub.3                                                                          F  H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           647                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           648                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           649                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           650                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           651                                                                               CF.sub.3                                                                          Cl H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           652                                                                               CF.sub.3                                                                          F  H CF.sub.3                                                                           Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           653                                                                               CF.sub.3                                                                          Cl H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           654                                                                               CF.sub.3                                                                          F  H CF.sub.3                                                                           F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           655                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H Cl  CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           658                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H F   CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           657                                                                               CF.sub.3                                                                          CF.sub.3                                                                          H CF.sub.3                                                                           CF.sub.3                                                                           CH.sub.2 cPr                                                                            Ph-4-OMe                                           658                                                                               CF.sub.3                                                                          F  F F   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           659                                                                               CF.sub.3                                                                          F  F F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           660                                                                               CF.sub.3                                                                          F  F Cl  F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           661                                                                               CF.sub.3                                                                          F  F Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           662                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -1-F-cPr                                                                       Ph                                                 663                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -2-F-cPr                                                                       Ph                                                 664                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph                                                 665                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -1-F-cPr                                                                       Ph-4-OMe                                           666                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -2-F-cPr                                                                       Ph-4-OMe                                           667                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph-4-OMe                                           668                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -1-F-cPr                                                                       Ph                                                 669                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -2-F-cPr                                                                       Ph                                                 670                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -2-F.sub.2 -cPr                                                                Ph                                                 671                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -1-F-cPr                                                                       Ph-4-OMe                                           672                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -2-F-cPr                                                                       Ph-4-OMe                                           673                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -2-F.sub.2 -cPr                                                                Ph-4-OMe                                           674                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -1-F-cPr                                                                       Ph                                                 675                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -2-F-cPr                                                                       Ph                                                 676                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph                                                 677                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -1-F-cPr                                                                       Ph-4-OMe                                           678                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -2-F-cPr                                                                       Ph-4-OMe                                           679                                                                               CF.sub.3                                                                          H  H Cl  F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph-4-OMe                                           680                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -1-F-cPr                                                                       Ph                                                 681                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -2-F-cPr                                                                       Ph                                                 682                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -2-F.sub.2 -cPr                                                                Ph                                                 683                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -1-F-cPr                                                                       Ph-4-OMe                                           684                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -2-F-cPr                                                                       Ph-4-OMe                                           685                                                                               CF.sub.3                                                                          H  H F   Cl  CH.sub.2 -2-F.sub.2 -cPr                                                                Ph-4-OMe                                           686                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -1-F-cPr                                                                       Ph                                                 687                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2-F-cPr                                                                       Ph                                                 688                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph                                                 689                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -1-F-cPr                                                                       Ph-4-OMe                                           690                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2-F-cPr                                                                       Ph-4-OMe                                           691                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2-F.sub.2 -cPr                                                                Ph-4-OMe                                           692                                                                               CF.sub.3                                                                          H  H H   Br  CH.sub.2 CH.sub.3                                                                       Ph                                                 693                                                                               CF.sub.3                                                                          H  H H   Br  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           694                                                                               CF.sub.3                                                                          H  H H   Br  CH.sub.2 -cPr                                                                           Ph        n.sub.D.sup.23.5 1.5343                  695                                                                               CF.sub.3                                                                          H  H H   Br  CH.sub.2 -cPr                                                                           Ph-4-OMe  n.sub.D.sup.23.5 1.5330                  696                                                                               CF.sub.3                                                                          H  H H   Br  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        697                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 CH.sub.3                                                                       Ph                                                 698                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           699                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 -cPr                                                                           Ph        114-115                                  700                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 -cPr                                                                           Ph-4-OMe  n.sub.D.sup.23.1 1.5304                  701                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 -cPr                                                                           Ph-4-F    81-82                                    702                                                                               CF.sub.3                                                                          H  H Cl  Br  CH.sub.2 CH.sub.3                                                                       Ph                                                 703                                                                               CF.sub.3                                                                          H  H Cl  Br  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           704                                                                               CF.sub.3                                                                          H  H Cl  Br  CH.sub.2 -cPr                                                                           Ph                                                 705                                                                               CF.sub.3                                                                          H  H Cl  Br  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           706                                                                               CF.sub.3                                                                          H  H Cl  Br  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        707                                                                               CF.sub.3                                                                          H  H Br  F   CH.sub.2 CH.sub.3                                                                       Ph                                                 708                                                                               CF.sub.3                                                                          H  H Br  F   CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           709                                                                               CF.sub.3                                                                          H  H Br  F   CH.sub.2 -cPr                                                                           Ph                                                 710                                                                               CF.sub.3                                                                          H  H Br  F   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           711                                                                               CF.sub.3                                                                          H  H Br  F   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        712                                                                               CF.sub.3                                                                          H  H Br  Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 713                                                                               CF.sub.3                                                                          H  H Br  Cl  CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           714                                                                               CF.sub.3                                                                          H  H Br  Cl  CH.sub.2 -cPr                                                                           Ph                                                 715                                                                               CF.sub.3                                                                          H  H Br  Cl  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           716                                                                               CF.sub.3                                                                          H  H Br  Cl  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        717                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 CH.sub.3                                                                       Ph                                                 718                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           719                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 -cPr                                                                           Ph        91-92                                    720                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 -cPr                                                                           Ph-4-OMe  109-110                                  721                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        722                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 CH.sub.3                                                                       Ph                                                 723                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 -cPr                                                                           Ph-2-F    94-95                                    724                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 -cPr                                                                           Ph         99-100                                  725                                                                               CF.sub.3                                                                          H  H F   H   CH.sub.2 -cPr                                                                           Ph-4-F    110-111                                  726                                                                               CF.sub.3                                                                          H  H Cl  H   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        727                                                                               CF.sub.3                                                                          H  H H   I   CH.sub.2 CH.sub.3                                                                       Ph                                                 728                                                                               CF.sub.3                                                                          H  H H   I   CH.sub.2 CH.sub.3                                                                       Ph-4-OMe                                           729                                                                               CF.sub.3                                                                          H  H H   I   CH.sub.2 -cPr                                                                           Ph                                                 730                                                                               CF.sub.3                                                                          H  H H   I   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           731                                                                               CF.sub.3                                                                          H  H H   I   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        732                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -cHxe-3                                                                        Ph        106-107                                  733                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -cHex-                                                                         Ph        124-125                                                     3,4-Br.sub.2                                                734                                                                               CF.sub.3                                                                          H  H Cl  Cl  CH.sub.2 -cHex                                                                          Ph        106-109                                  735                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 -cPr                                                                           Ph                                                 736                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           737                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        738                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 739                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 CH.sub.3                                                                       Ph                                                 740                                                                               C.sub.2 F.sub.5                                                                   H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 741                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph                                                 742                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           743                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        744                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 745                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 746                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 747                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 -cPr                                                                           Ph                                                 748                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           749                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        750                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 751                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 752                                                                               C.sub.2 F.sub.5                                                                   H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 753                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 -cPr                                                                           Ph                                                 754                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           755                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        756                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 757                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 CH.sub.3                                                                       Ph                                                 758                                                                               C.sub.2 F.sub.5                                                                   H  H Cl  F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 759                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 -cPr                                                                           Ph                                                 760                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           761                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        762                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 763                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 CH.sub.3                                                                       Ph                                                 764                                                                               CCl.sub.3                                                                         H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 765                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph                                                 766                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           767                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        768                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 769                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 770                                                                               CCl.sub.3                                                                         H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 771                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 -cPr                                                                           Ph                                                 772                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 -cPr                                                                           Ph-4-OMe                                           773                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        774                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 775                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 776                                                                               CCl.sub.3                                                                         H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 777                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 -cPr                                                                           Ph                                                 778                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 -cPr                                                                           Ph-4-OMe                                           779                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 -cPr                                                                           Ph-2-F-5-Me                                        780                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 781                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 CH.sub.3                                                                       Ph                                                 782                                                                               CCl.sub.3                                                                         H  H Cl  F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 783                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 cPr                                                                            Ph                                                 784                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           785                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        786                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 787                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 CH.sub.3                                                                       Ph                                                 788                                                                               CHF.sub.2                                                                         H  H F   F   CH.sub.2 C.tbd.CH                                                                       Ph                                                 789                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph                                                 790                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           791                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        792                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 793                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 794                                                                               CHF.sub.2                                                                         H  H Cl  Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 795                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 cPr                                                                            Ph                                                 796                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 cPr                                                                            Ph-4-OMe                                           797                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        798                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 799                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 CH.sub.3                                                                       Ph                                                 800                                                                               CHF.sub.2                                                                         H  H F   Cl  CH.sub.2 C.tbd.CH                                                                       Ph                                                 801                                                                               CHF.sub.2                                                                         H  H Cl  F   CH.sub.2 cPr                                                                            Ph                                                 802                                                                               CHF.sub.2                                                                         H  H Cl  F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           803                                                                               CHF.sub.2                                                                         H  H Cl  F   CH.sub.2 cPr                                                                            Ph-2-F-5-Me                                        804                                                                               CHF.sub.2                                                                         H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 805                                                                               CHF.sub.2                                                                         H  H Cl  F   CH.sub.2 CH.sub.2 Cl                                                                    Ph                                                 806                                                                               CHF.sub.2                                                                         H  H Cl  G   CH.sub.2 C.tbd.CH                                                                       Ph                                                 807                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CF.sub.3                                                                       Ph                                                 808                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 Cl                                                                             Ph                                                 809                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 Br                                                                    Ph                                                 810                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 OEt                                                                            Ph                                                 811                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 OMe                                                                   Ph                                                 812                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPent                                                                          Ph                                                 813                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cHex                                                                           Ph                                                 814                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr-2,2-                                                                       Ph                                                                    Cl.sub.2                                                    815                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr-2,2-                                                                       Ph                                                                    Br.sub.2                                                    816                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 SMe                                                                            Ph        n.sub.D.sup.23.2 1.5469                  817                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 SOMe                                                                           Ph        n.sub.D.sup.26.0 1.5462                  818                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 SO.sub.2 Me                                                                    Ph        116-117                                  819                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CO.sub.2 Me                                                                    Ph        n.sub.D.sup.22.8 1.5194                  820                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CO.sub.2 Et                                                                    Ph        n.sub.D.sup.22.8 1.5167                  821                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 CO.sub.2 Me                                                           Ph                                                 822                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 NMe.sub.2                                                                      Ph                                                 823                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 NHMe                                                                           Ph                                                 824                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 NMe.sub.2                                                             Ph                                                 825                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CONH.sub.2                                                                     Ph        n.sub.D.sup.24.5 1.5380                  826                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CONHMe                                                                         Ph                                                 827                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CONMe.sub.2                                                                    Ph        n.sub.D.sup.23.3 1.5302                  828                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CHCF.sub.3                                                              Ph                                                 829                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH═CF.sub.2                                                                Ph                                                 830                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 C(Br)═CH.sub.2                                                             Ph                                                 831                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CCH.sub.3                                                                Ph                                                 832                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 CH.sub.2 C.tbd.CH                                                              Ph                                                 833                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 C.tbd.CCF.sub.3                                                                Ph                                                 834                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CF.sub.3                                                                       Ph                                                 835                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 Cl                                                                             Ph                                                 836                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 Br                                                                    Ph                                                 837                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CEt                                                                            Ph                                                 838                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 OMe                                                                   Ph                                                 839                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPent                                                                          Ph                                                 840                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cHex                                                                           Ph                                                 841                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2,2-Cl.sub.2 -                                                                Ph                                                                    cPr                                                         842                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 -2,2-Br.sub.2 -                                                                Ph                                                                    cPr                                                         843                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 SMe                                                                            Ph                                                 844                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 SOMe                                                                           Ph                                                 845                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 SO.sub.2 Me                                                                    Ph                                                 846                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CO.sub.2 Me                                                                    Ph                                                 847                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CO.sub.2 Et                                                                    Ph        n.sub.D.sup.24.0 1.5066                  848                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 CO.sub.2 Me                                                           Ph                                                 849                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 NMe.sub.2                                                                      Ph                                                 850                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 NHMe                                                                           Ph                                                 851                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 NMe.sub.2                                                             Ph                                                 852                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CONH.sub.2                                                                     Ph                                                 853                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CONHMe                                                                         Ph                                                 854                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CONMe.sub.2                                                                    Ph                                                 855                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CHC═CHCF.sub.3                                                             Ph                                                 856                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH═CF.sub.2                                                                Ph                                                 857                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C(Br)═CH.sub.2                                                             Ph                                                 858                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CCH.sub.3                                                                Ph                                                 859                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 CH.sub.2 C.tbd.CH                                                              Ph                                                 860                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 C.tbd.CCF.sub.3                                                                Ph                                                 861                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-Cl   82-83                                    862                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-Br   89-90                                    863                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-Cl-4-F                                        864                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-2-Br-4-Me                                       865                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-Et                                            866                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OEt                                           867                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OiPr                                          868                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCH.sub.2 CH═CH.sub.2                                                           65-67                                    869                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCH.sub.2 C.tbd.CH                                                                  77-78                                    870                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-3-CF.sub.3                                                                            77-78                                    871                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-CF.sub.3                                                                            124-125                                  872                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-CF.sub.2 CF.sub.2 H                           873                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.3                                                                           96-97                                    874                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 H                                   875                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 CF.sub.3                            876                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 CF.sub.2 H                          877                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            1-Me-2-Pyrrolyl                                    878                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            1-Me-3-Pyrrolyl                                    879                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            2-Pyrrolyl                                         880                                                                               CF.sub.3                                                                          H  H H   F   CH.sub.2 cPr                                                                            3-Pyrrolyl                                         881                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2-Cl                                            882                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-Br                                            883                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2-Cl-4-F                                        884                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-2-Br-4-CH.sub.3                                 885                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-Et                                            886                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OEt                                           887                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OiPr                                          888                                                                               CF.sub.3                                                                          H  H P   F   CH.sub.2 cPr                                                                            Ph-4-OCH.sub.2 CH═CH.sub.2                     889                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OCH.sub.2 C.tbd.CH                            890                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-3-CF.sub.3                                      891                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-CF.sub.3                                      892                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-CF.sub.2 CF.sub.2 H                           893                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.3                                     894                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 H                                   895                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 CF.sub.3                            896                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            Ph-4-OCF.sub.2 CF.sub.2 H                          897                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-Me-2-Pyrrolyl                                    898                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-Me-3-Pyrrolyl                                    899                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-Pyrrolyl                                         900                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-Pyrrolyl                                         901                                                                               CF.sub.3                                                                          H  H F   Br  CH.sub.2 cPr                                                                            Ph        n.sub.D.sup.22.0 1.5349                  902                                                                               CF.sub.3                                                                          H  H H   Et  CH.sub.2 cPr                                                                            Ph                                                 903                                                                               CF.sub.3                                                                          H  H H   nPr CH.sub.2 cPr                                                                            Ph                                                 904                                                                               CF.sub.3                                                                          H  H H   nBu CH.sub.2 cPr                                                                            Ph                                                 905                                                                               CF.sub.3                                                                          H  H H   tBu CH.sub.2 cPr                                                                            Ph                                                 906                                                                               CF.sub.3                                                                          H  H H   C.sub.2 F.sub.5                                                                    CH.sub.2 cPr                                                                            Ph                                                 907                                                                               CF.sub.3                                                                          H  H H   OEt CH.sub.2 cPr                                                                            Ph                                                 908                                                                               CF.sub.3                                                                          H  H H   OnPr                                                                               CH.sub.2 cPr                                                                            Ph                                                 909                                                                               CF.sub.3                                                                          H  H H   OiPr                                                                               CH.sub.2 cPr                                                                            Ph                                                 910                                                                               CF.sub.3                                                                          H  H H   OtBu                                                                               CH.sub.2 cPr                                                                            Ph                                                 911                                                                               CF.sub.3                                                                          H  H OEt F   CH.sub.2 cPr                                                                            Ph                                                 912                                                                               CF.sub.3                                                                          H  H OnPr                                                                               F   CH.sub.2 cPr                                                                            Ph                                                 913                                                                               CF.sub.3                                                                          H  H OiPr                                                                               F   CH.sub.2 cPr                                                                            Ph                                                 914                                                                               CF.sub.3                                                                          H  H OtBu                                                                               F   CH.sub.2 cPr                                                                            Ph                                                 915                                                                               CF.sub.3                                                                          H  H H   SOMe                                                                               CH.sub.2 cPr                                                                            Ph        n.sub.D.sup.23.3 1.5450                  916                                                                               CF.sub.3                                                                          H  H H   SO.sub.2 Me                                                                        CH.sub.2 cPr                                                                            Ph        144-146                                  917                                                                               CF.sub.3                                                                          H  H H   SEt CH.sub.2 cPr                                                                            Ph                                                 918                                                                               CF.sub.3                                                                          H  H H   S-iPr                                                                              CH.sub.2 cPr                                                                            Ph                                                 919                                                                               CF.sub.3                                                                          H  H SOMe                                                                               F   CH.sub.2 cPr                                                                            Ph                                                 920                                                                               CF.sub.3                                                                          H  H SO.sub.2 Me                                                                        F   CH.sub.2 cPr                                                                            Ph                                                 921                                                                               CF.sub.3                                                                          H  H SEt F   CH.sub.2 cPr                                                                            Ph                                                 922                                                                               CF.sub.3                                                                          H  H S-iPr                                                                              F   CH.sub.2 cPr                                                                            Ph                                                 923                                                                               CF.sub.3                                                                          H  H OCF.sub.3                                                                          F   CH.sub.2 cPr                                                                            Ph-4-OMe                                           924                                                                               CF.sub.3                                                                          H  H OCF.sub.3                                                                          F   CH.sub.2 cPr                                                                            Ph-2-F                                             925                                                                               CF.sub.3                                                                          H  H OCF.sub.3                                                                          F   CH.sub.2 cPr                                                                            Ph-4-F                                             926                                                                               CF.sub.3                                                                          H  H OCF.sub.3                                                                          F   CH.sub.2 cPr                                                                            Ph                                                 927                                                                               CF.sub.3                                                                          H  H NO.sub.2                                                                           OCH.sub.3                                                                          CH.sub.2 cPr                                                                            Ph                                                 928                                                                               CF.sub.3                                                                          H  H NHAc                                                                               F   CH.sub.2 cPr                                                                            Ph                                                 929                                                                               CF.sub.3                                                                          H  H NH.sub.2                                                                           F   CH.sub.2 cPr                                                                            Ph                                                 930                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 COOH                                                                           Ph        113-120                                  931                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-imidazolyl                                       932                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-methyl-2-                                                                    imidazolyl                                         933                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-methyl-2-                                                                    oxazolyl                                           934                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-isoxazolyl                                       935                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-methyl-2-                                                                    isoxazolyl                                         936                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-pyrimidinyl                                      937                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            4,6-dimethyl-2-                                    pyrimidinyl                                                                    938                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-thiazolyl                                        939                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-chloro-2-                                        thiazolyl                                                                      940                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            1-pyrazinyl                                        941                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-mrthyl-1-                                                                    pyrazinyl                                          942                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-pyridazinyl                                      943                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-methyl-4-                                                                    pyridazinyl                                        944                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            2-furyl                                            945                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            3-bromo-2-                                                                     furyl                                              946                                                                               CF.sub.3                                                                          H  H F   F   CH.sub.2 cPr                                                                            4-thiazolyl                                        __________________________________________________________________________      ##STR12##

                                      TABLE 4                                      __________________________________________________________________________                                                  Physical const.                                                                mp. (° C.)/                No. X.sup.1                                                                            X.sup.2                                                                           X.sup.3                                                                           X.sup.4                                                                            X.sup.5                                                                            R.sup.1 r.sub.1                                                                             r.sub.2                                                                            R.sup.2                                                                              refractive                        __________________________________________________________________________                                                  index                             947 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           OMe  H   Ph    25.4-1.5069                       948 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           Me   H   Ph    25.5-1.5106                       949 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           Et   H   Ph    25.4-1.5003                       950 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           OMe  CF.sub.3                                                                           Ph    25.5-1.4855                       951 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           F    H   Ph    25.5-1.5059                       952 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           Cl   H   Ph    25.5-1.5244                       953 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           SMe  H   Ph    25.5-1.5220                       954 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           ═O   Ph    79-81                             955 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           Me   Me  Ph    25.6-1.5105                       956 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           F    F   Ph    50-52                             957 CF.sub.3                                                                           H  H  F   F   CH.sub.2 cPr                                                                           NHMe H   Ph                                      958 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           OMe  H   Ph                                      959 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           Me   H   Ph                                      960 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           Et   H   Ph                                      961 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           OMe  CF.sub.3                                                                           Ph                                      962 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           F    H   Ph                                      963 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           Cl   H   Ph                                      964 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           SMe  H   Ph                                      965 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           ═O   Ph                                      966 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           Me   Me  Ph                                      967 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           F    F   Ph                                      968 CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 cPr                                                                           NHMe H   Ph                                      969 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           OMe  H   Ph                                      970 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           Me   H   Ph                                      971 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           Et   H   Ph                                      972 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           OMe  CF.sub.3                                                                           Ph                                      973 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           F    H   Ph                                      974 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           Cl   H   Ph                                      975 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           SMe  H   Ph                                      976 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           ═O   Ph                                      977 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           Me   Me  Ph                                      978 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           F    F   Ph                                      979 CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 cPr                                                                           NHMe H   Ph                                      980 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           OMe  H   Ph                                      981 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           Me   H   Ph                                      982 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           Et   H   Ph                                      983 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           OMe  CF.sub.3                                                                           Ph                                      984 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           F    H   Ph                                      985 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           Cl   H   Ph                                      986 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           SMe  H   Ph                                      987 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           ═O   Ph                                      988 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           Me   Me  Ph                                      989 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           F    F   Ph                                      990 CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 cPr                                                                           NHMe H   Ph                                      991 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           OMe  H   Ph                                      992 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           Me   H   Ph                                      993 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           Et   H   Ph                                      994 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           OMe  CF.sub.3                                                                           Ph                                      995 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           F    H   Ph                                      996 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           Cl   H   Ph                                      997 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           SMe  H   Ph                                      998 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           ═O   Ph                                      999 CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           Me   Me  Ph                                      1000                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           F    F   Ph                                      1001                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 cPr                                                                           NHMe H   Ph                                      1002                                                                               CF.sub.3                                                                           H  H  F   F   Et      Me   H   Ph                                      1003                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph                                      1004                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph                                      1005                                                                               CF.sub.3                                                                           H  H  F   F   Et      Me   H   Ph-4-OMe                                1006                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph-4-OMe                                1007                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph-4-OMe                                1008                                                                               CF.sub.3                                                                           H  H  F   Cl  Et      Me   H   Ph                                      1009                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 C.tbd.CH                                                                      Me   H   Ph                                      1010                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph                                      1011                                                                               CF.sub.3                                                                           H  H  F   Cl  Et      Me   H   Ph-4-OMe                                1012                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 C.tbd.CH                                                                      Me   H   Ph-4-OMe                                1013                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph-4-OMe                                1014                                                                               CF.sub.3                                                                           H  H  Cl  F   Et      Me   H   Ph                                      1015                                                                               CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph                                      1016                                                                               CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph                                      1017                                                                               CF.sub.3                                                                           H  H  Cl  F   Et      Me   H   Ph-4-OMe                                1018                                                                               CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph-4-OMe                                1019                                                                               CF.sub.3                                                                           H  H  Cl  F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph-4-OMe                                1020                                                                               CF.sub.3                                                                           H  H  Cl  Cl  Et      Me   H   Ph                                      1021                                                                               CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 C.tbd.CH                                                                      Me   H   Ph                                      1022                                                                               CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph                                      1023                                                                               CF.sub.3                                                                           H  H  Cl  Cl  Et      Me   H   Ph-4-OMe                                1024                                                                               CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 C.tbd.CH                                                                      Me   H   Ph-4-OMe                                1025                                                                               CF.sub.3                                                                           H  H  Cl  Cl  CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph-4-OMe                                1026                                                                               CF.sub.3                                                                           H  H  H   F   Et      Me   H   Ph                                      1027                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph                                      1028                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph                                      1029                                                                               CF.sub.3                                                                           H  H  H   F   Et      Me   H   Ph-4-OMe                                1030                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 C.tbd.CH                                                                      Me   H   Ph-4-OMe                                1031                                                                               CF.sub.3                                                                           H  H  H   F   CH.sub.2 CH.sub.2 Cl                                                                   Me   H   Ph-4-OMe                                1032                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 CN                                                                            H    H   Ph    77-80                             1033                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 CN                                                                            H    H   Ph                                      1034                                                                               CF.sub.3                                                                           H  H  F   F   CH.sub.2 CH(OEt).sub.2                                                                 H    H   Ph                                      1035                                                                               CF.sub.3                                                                           H  H  F   Cl  CH.sub.2 CH(OEt).sub.2                                                                 H    H   Ph                                      1036                                                                               CF.sub.3                                                                           H  H  NO.sub.2                                                                           OEt CH.sub.2 cPr                                                                           H    H   Ph    62-63                             __________________________________________________________________________      *25.4-1.5069 means n.sub.D.sup.25.4 1.5069 (refractive index) in the abov      tables.                                                                        .sup.1 HNMR data (CDCl.sub.3, δ ppm from TMS);                           *1 Compound No. 346                                                            0.1˜0.2(2H, m), 0.45˜0.55(2H, m), 0.95˜1.1(1H, m),           3.60(2H, s), 3.8˜3.9(2H, m), 3.82(3H, s), 6.92(2H, d),                   7.1˜7.25(3H, m), 7.51(1H, dd), 8.53(1H, brs)                       

The compounds of the present invention can show excellent fungicidal activity against wide varieties of fungi, and therefore, the compounds can be useful for plant disease control in the farming of agricultural and horticultural crops including ornamental flowers, turf and forage crops.

The examples for the plant diseases to be controlled with the compounds of the present invention are given in the following.

    ______________________________________                                         Paddy rice                                                                            Blast           (Pyricularia oryzae)                                           Sheath blight   (Rhizoctonia solani)                                           Bakanae disease (Gibberella fujikuroi)                                         Helminthosporium leaf spot                                                                     (Cochliobolus miyabeanus)                               Barley Loose smut      (Ustilago nuda)                                         Wheat  Scab            (Gibberella zeae)                                              Leaf rust       (Puccinia recondita)                                           Eye spot        (Pseudocercosporella                                                           herpotrichoides)                                               Glume blotch    (Leptosphaeria nodorum)                                        Powdery mildew  (Erysiphe graminis f sp. tritici)                              Fusarium snow blight                                                                           (Micronectriella nivalis)                               Potato Late blight     (Phytophthora infestans)                                Ground Leaf spot       (Mycosphaerella aradius)                                nut                                                                            Sugar beat                                                                            Cercospora leaf (Cercospora beticola)                                          spot                                                                    Cucumber                                                                              Powdery mildew  (Sphaerotheca fuliginea)                                       Sclerotinia rot (Sclerotinia sclerotiorum)                                     Gray mold       (Botrytis cinerea)                                             Downy mildew    (Pseudoperonospora cubensis)                            Tomato Leaf nold       (Cladosporium fulvum)                                          Late blight     (Phytophthora infestans)                                Egg plant                                                                             Black rot       (Corynespora melongenae)                                Onion  Gray-mold neck rot                                                                             (Botrytis allii)                                        Straw- Powdery mildew  (Sphaerotheca humuli)                                   berry                                                                          Apple  Powdery mildew  (Podosphaera leucotricha)                                      Scab            (Venturia inaequalis)                                          Blossow blight  (Monilinia mali)                                        Per-   Anthracnose     (Gloeosporium kaki)                                     simmon                                                                         Peach  Brown rot       (Monilinia fructicola)                                  Grape  Powdery mildew  (Uncinula necator)                                             Downy mildew    (Plasmopara viticola)                                   Pear   Rust            (Gymnosporangium asiaticum)                                    Black spot      (Alternaria kikuchiana)                                 Tea-plant                                                                             Leaf spot       (Pestalotia theae)                                             Anthracnose     (Colletotrichum theae-sinensis)                         Orange Scab            (Elsinoe fawcetti)                                             Blue mlold      (Penicillium italicum)                                  Turf   Sclerotinia snow blight                                                                        (Sclerotinia borealis)                                  ______________________________________                                    

In recent years, it is known that various pathogenic fungi have developed their resistance to benzimidazole fungicides and ergosterol biosynthesis inhibitors and that such fungicides have been insufficient in their fungicidal effectiveness. Therefore, it is required to provide new compounds useful as a fungicide which are effective to the resistant-strain of such pathogenic fungi as well. The compounds of the present invention are the ones which can be a fungicide having excellent fungicidal effectiveness not only to the susceptible-strains of pathogenic fungi but also to the resistant-strains of pathogenic fungi to benzimidazole fungicides and ergosterol biosynthesis inhibitors.

For the preferable examples of plant diseases to be applied with the compounds of the present invention, powdery mildew on wheat, powdery mildew on cucumber, powdery mildew on strawberries, etc. can be given.

The compounds of the present invention can be utilized as an antifouling agent for preventing the adhesion of aqueous organisms to structures, such as the bottom of a ship and fishing nets, in water and sea.

Also, the compounds of the present invention can be contained in paints and fibers and thereby used as an antimicrobial agent for walls, bathtubs, shoes and clothes.

Furthermore, some of the compounds of the present invention can show insecticidal, acaricidal and herbicidal activities.

In the practical application of the compounds of the present invention obtained as described above, the compounds can be used in the state as it is without formulation, or, for the use as agricultural plant protection chemicals, the compounds can be applied in forms of general formulations for agricultural plant protection chemicals, such as wettable powders, granules, powders, emulsifiable concentrates, aqueous solutions, suspensions and flowables. For the additives and carriers to be used in the formulations described above, vegetable powders, such as soybean powder and wheat powder, mineral fine powders, such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds, such as sodium benzoate, urea and Glauber's salt, can be used, when the compounds are formulated into solid formulations. Whereas, when the compounds are formulated into liquid formulations, petroleum fractions, such as kerosine, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethyl formamide, dimethyl sulfoxide, alcohols, acetone, trichloro ethylene, methylisobutyl ketone, mineral oils, vegetable oils and water, can be used as the solvent. In these formulations, surface active agents may be added to the formulations in order to make the formulations homogeneous and stable, if appropriate.

The content of the compound of the present invention as the active principle in the formulations is preferably in a range of from 5 to 70%.

The wettable powders, the emulsifiable concentrates and the flowable formulation comprising the compound of the present invention prepared as described above can be applied in a form prepared by diluting the formulations with water to the suspension or the emulsion at a desired concentrations, while the powders and the granules of the said compound can be directly applied to plants without dilution.

The compounds of the present invention can demonstrate sufficient effectiveness on plant diseases independently, however, it is also possible to use the said compound in admixing with 1 or more of other fungicides, insecticides, acaricides or synergists.

The followings are the examples for the fungicides, insecticides, acaricides, nematocides and plant growth regulators, those which are usable in admixing with the compounds of the present invention.

Fungicides

Copper-Based Fungicides

Basic copper chloride, basic copper sulfate, etc.

Sulphur-based Fungicides

Thiram, maneb, mancozeb, polycarbamate, propineb, ziram, zineb, etc.

Polyhaloalkylthio Fungicides

Captan, dichlofluanid, folpet, etc.

Organochlorine Fungicides

Chlorothalonil, fthalide, etc.

Organophosphorous Fungicides

IBP, EDDP, tolclofos-methyl, pyrazophos, fosetyl-Al, etc.

Benzimidazole Fungicides

Thiophanate-methyl, benomyl, carbendazim, thiabendazole, etc.

Dicarboxyimide Fungicides

Oxycarboxine, mepronyl, flutolanil, techlofthalam, trichlamide, pencycuron, etc.

Acyl Alanine Fungicides

Metalaxyl, oxadixyl, furalaxyl etc.

EBI Fungicides

Triadimefon, triadomenol, bitertanol, microbutanil, hexaconazol, propiconazole, triflumizole, procloraz, peflazoate, fenarimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazol, fluotrimazole, flutriafen, penconazole, diniconazole, cyproconazole, imazalil, tridemorph, fenpropimorph, buthiobate, etc.

Antibiotics

Polyoxin, blasticidin-S, kasugamycin, validamycin, streptomycin sulfate, etc.

Others

Propamocarb hydrochloride salt, quintozene, hydroxyisoxazole, metasulfocarb, anilazine, isoprothiolane, probenazole, quinomethionate, dithianone, dinocap, dichlomezine, mepaniprim, ferimzone, fluazinam, pyroquilon, tricyclazole, oxolinic acid, dithianone, iminoctazine acetate salt, cymoxanil, pyrrolenitrine, metasulfocarb, diethofencarb, binapacryl, lecithin, sodium hydrogencarbonate, fenaminosulf, dodine, dimethomorph, fenazine oxide, etc.

Insecticides and Acaricides

Organophosphorous and Carbamate Insecticides

Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, fenthoate, dimethoate, formothion, malathon, trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimeton methyl, ethion, salithion, cyanophos, isoxathion, pyridafenthion, phosalon, methydathion, sulprofos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos, pyraclophos, monocrotophos, azinphos methyl, aldicarb, methomyl, thiodicarb, carbofuran, carbosulfan, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, cartap, thiocyclam, bensultap, etc.

Pyrethroid Insecticides

Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propathrin, fenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate, ethofenprox, cycloprothrin, tralomethrin, silafluophen, brofenprox, acrinathrin, etc.

Benzoyl Urea-Based Insecticides and Others:

Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diaphenthiuron, imidacloprid, fipronil, nicotine sulfate, rotenone, meta-aldehyde, machine oil, Bacillus thuringiensis, microbial insecticides such as insect-pathogenic viruses, etc.

Nematocides

Fenamiphos, phosthiazate, etc.

Acaricides

Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexythiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradifon, avermectin, milbemectin, chlofentezin, cyhexatin, pyridaben, fenpyroxymate, tebufenpyrad, pyrimidifen, fenothiocarb, dienochlor, etc.

Plant Growth Regulators

Gibberellines (Gibberelline A₃, Gibberelline A₄, Gibberelline A₇, etc.), IAA, and NAA.

Now, the examples of the formulations comprising the compound of the present invention are described hereinbelow, however, it should be noted that the type and the rate of the additives shall not be limited to the ones described in the examples and can be replaced by wide range of other additives and/or carriers. In the examples hereinbelow, a part mentioned in each of the formulation examples represents a part by weight.

EXAMPLE 3

Wettable Powder

    ______________________________________                                         The compound of the present invention                                                                    40    parts                                          Diatomaceous earth        53    parts                                          Sulfuric acid ester of higher alcohol                                                                    4     parts                                          Alkyl naphthalene sulfonate                                                                              3     parts                                          ______________________________________                                    

All components are admixed and micronized to fine powder, thereby affording the wettable powder formulation containing the active principle at a concentration of 40%.

EXAMPLE 4

Emulsifiable Concentrate

    ______________________________________                                         The compound of the present invention                                                                    30    parts                                          Xylene                    33    parts                                          Dimethyl formamide        30    parts                                          Polyoxy ethlene alkylally ether                                                                          7     parts                                          ______________________________________                                    

All components are admixed and then dissolved into a solution. thereby affording the emulsifiable concentrate formulation containing the active principle at a concentration of 30%.

EXAMPLE 5

Dust Formulation

    ______________________________________                                         The compound of the present invention                                                                    10    parts                                          Talc                      89    parts                                          Polyoxy ethlene alkylally ether                                                                          1     parts                                          ______________________________________                                    

All components are admixed and pulverized to fine dusting powder, thereby affording the dust formulation containing the active principle at a concentration of 10%.

EXAMPLE 6

Granular Formulation

    ______________________________________                                         The compound of the present invention                                                                    5     parts                                          Clay                      73    parts                                          Bentonite                 20    parts                                          Sodium salt of dioctylsulfosuccinate                                                                     1     part                                           Sodium phosphate          1     part                                           ______________________________________                                    

All components are admixed, pulverized and then kneaded thoroughly while adding water, and then further granulated and dried, thereby affording the granular formulation containing the active principle at a concentration of 5%.

EXAMPLE 7

Suspension

    ______________________________________                                         The compound of the present invention                                                                   10     parts                                          Sodium lignin sulfonate  4      parts                                          Sodium dodecyl benzene sulfonate                                                                        1      part                                           Xanthane Gum             0.2    part                                           Water                    84.8   parts                                          ______________________________________                                    

All components are admixed and subjected to wet grinding up to the particle size of less than 1μ, thereby affording the suspension containing the active principle at a concentration of 10%.

Now, the usefulness of the compounds of the present invention as the active principle of a plant protection chemical for controlling various plant diseases is shown in Test Examples described hereinbelow. The effectiveness of the compounds on plant disease control were assessed basing on the pathological changes in the state of plants provided, namely the degree of disease-induced lesion on leaves, stems and other parts of the plants was visually observed, respectively. The assessment was conducted by giving scores in effectiveness on plant diseases to each test plots as the following.

Score, 5; If no lesion were observed.

Score, 4; If the degree of the lesion observed were approximately 10% of the degree in the untreated plot.

Score, 3; If the degree of the lesion observed were approximately 25% of the degree in the untreated plot.

Score, 2; If the degree of the lesion observed were approximately 50% of the degree in the untreated plot.

Score, 1; If the degree of the lesion observed were approximately 75% of the degree in the untreated plot.

Score, 0; If the degree of the lesion observed were almost same as the degree in the untreated plot.

Test Example 1 Preventive Control Efficacy Test on Wheat Powdery Mildew

To young seedlings of wheat (Variety: Chihoku) grown in an unglazed pot, the emulsion at a concentration of 12.5 ppm prepared from the emulsifiable concentrate comprising the compound of the present invention were sprayed throughly. After the spraying, the seedlings were dried under natural condition and then inoculated by means of sprinkling with the conidia of the fungus causing wheat powdery mildew (Erysiphe graminia f. sp. tritici) and placed in a greenhouse maintained at around 20° C. for 7 days in order to complete the infection. Appearance of the lesion on leaves cause by the disease was assessed and compared with the lesion on leaves in the untreated plot, thereby evaluating the preventive efficacy of the compound to the disease. The results are shown in Table 5.

Test Example 2 Preventive Control Efficacy Test on Cucumber Powdery Mildew

To young seedlings of cucumber (Variety: Sagami-Hanjiro) grown in an unglazed pot, the emulsion at a concentration of 12.5 ppm prepared from the emulsifiable concentrate comprising the compound of the present invention were sprayed. After the spraying, the seedlings were dried under natural condition and then inoculated by means of sprinkling with the conidia of the fungus causing cucumber powdery mildew (Sphaerotheca fuliginea) and placed in a temperature-controlled room maintained at around 25° C. for 11 days in order to complete the infection. Appearance of powdery mildew-causing lesion on the leaves whereto the compound was sprayed was assessed and compared with the lesion appeared on leaves in the untreated plot, thereby evaluating the preventive efficacy of the compound to the disease. The results are shown in Table 5.

As shown in Table 5, it is demonstrated that the compounds of the present invention can show superior preventive control efficacy to not only wheat powdery mildew but also cucumber powdery mildew in comparison with other compounds tested.

Test Example 3 Test on Cucumber Powdery Mildew Control with Vapour

10 μl of the emulsion at a concentration of 500 ppm prepared from the emulsifiable concentrate comprising the compound of the present invention were fed dropwise onto round aluminium foils each having a diameter of 1 cm and dried at room temperature under natural condition.

The aluminium foils were then fixed on the upper side of the leaves of cucumber seedlings (Variety: Sagami-Hanjiro) grown in an unglazed pot. After 24 hours, the cucumber leaves were inoculated by means of sprinkling with the conidia of the fungus causing cucumber powdery mildew (Sphaerotheca fuliginea) and placed in a temperature-controlled room maintained at around 25° C. for 11 days in order to complete the infection. Appearance of powdery mildew-causing lesion on the leaves placed with the aluminium foil was assessed and compared with the lesion appeared on the leaves in the untreated plot. The control efficacy with the vapour of the compound to the disease was confirmed in case that disease lesion-free circle having a diameter of more than 2 cm is formed around the aluminium foil fixed on a leaf. The results are shown in Table 5.

On the other hand, other compounds for the comparison, which are disclosed in Japanese Patent Laid-opened No. Hei 2-6453 (see Table 5), did not show the control efficacy with the vapour to the disease.

Since the compounds of the present invention have vapour action, it is suggested that the compound of the present invention can show plant disease control efficacy even in the inner space of leaves and fruits of crops whereto spraying of a fungicide in even condition is generally rather difficult.

                  TABLE 5                                                          ______________________________________                                                Concentration                                                                  of active  Wheat      Cucumber                                                 ingredient Powdery    Powdery                                                                               Vapar                                      No.    (ppm)      mildew     mildew action                                     ______________________________________                                         1      12.5       5          5                                                 3      12.5       5          5                                                 4      12.5       5          5                                                 5      12.5       5          5                                                 6      12.5       5          5                                                 7      12.5       4          5                                                 8      12.5       5          5                                                 9      12.5       5          5                                                 10     12.5       4          5                                                 11     12.5       5          5                                                 12     12.5       5          5                                                 13     12.5       5          5                                                 18     12.5       2          4                                                 19     12.5       4          5                                                 20     12.5       4          5                                                 22     12.5       5          5                                                 24     12.5       5          5      good                                       25     12.5       5          5                                                 27     12.5       5          5                                                 28     12.5       4          4                                                 29     12.5       4          4                                                 30     12.5       5          4                                                 32     12.5       4          4                                                 33     12.5       3          5                                                 34     12.5       4          5      good                                       35     12.5       5          5      good                                       36     12.5       5          4                                                 37     12.5       4          5      good                                       38     12.5       5          4                                                 39     12.5       5          5      good                                       42     12.5       5          5      good                                       43     12.5       5          5      good                                       44     12.5       5          5      good                                       45     12.5       4          4                                                 46     12.5       5          5                                                 47     12.5       5          5      good                                       48     12.5       5          5      good                                       49     12.5       5          5                                                 50     12.5       5          5      good                                       51     12.5       5          5      good                                       52     12.5       5          5      good                                       53     12.5       5          5                                                 54     12.5       5          5      good                                       55     12.5       5          5                                                 56     12.5       5          5      good                                       57     12.5       5          5      good                                       58     12.5       4          4                                                 59     12.5       4          4                                                 60     12.5       4          5                                                 62     12.5       4          5                                                 64     12.5       4          4                                                 65     12.5       5          5                                                 66     12.5       5          5                                                 68     12.5       5          5                                                 71     12.5       5          4                                                 74     12.5       5          5                                                 82     12.5       5          5                                                 96     12.5       5          5      good                                       99     12.5       5          5      good                                       105    12.5       5          5      good                                       112    12.5       5          5      good                                       113    12.5       5          5      good                                       114    12.5       4          5                                                 115    12.5       4          5                                                 140    12.5       3          5      good                                       149    12.5       5          5      good                                       156    12.5       5          5      good                                       157    12.5       5          5      good                                       209    12.5       4          4                                                 211    12.5       4          4                                                 212    12.5       5          5                                                 234    12.5       5          5      good                                       239    12.5       5          5      good                                       240    12.5       5          5      good                                       241    12.5       5          5      good                                       242    12.5       5          5      good                                       255    12.5       5          5      good                                       258    12.5       5          5      good                                       260    12.5       5          5      good                                       262    12.5       5          5      good                                       263    12.5       5          5                                                 264    12.5       5          5      good                                       266    12.5       5          5                                                 267    12.5       5          5      good                                       268    12.5       5          5                                                 269    12.5       5          5      good                                       270    12.5       5          5      good                                       271    12.5       5          5                                                 272    12.5       5          5      good                                       273    12.5       5          5      good                                       274    12.5       5          5                                                 275    12.5       5          5                                                 276    12.5       5          4                                                 277    12.5       5          5                                                 279    12.5       5          5      good                                       280    12.5       5          5                                                 286    12.5       5          5                                                 287    12.5       5          5                                                 288    12.5       5          5                                                 289    12.5       5          5                                                 290    12.5       5          5      good                                       293    12.5       4          5                                                 304    12.5       5          5                                                 307    12.5       5          5                                                 309    12.5       5          5      good                                       311    12.5       5          5      good                                       312    12.5       5          5                                                 313    12.5       5          5      good                                       315    12.5       5          5                                                 316    12.5       5          5                                                 319    12.5       5          5      good                                       320    12.5       5          5                                                 321    12.5       5          5                                                 322    12.5       5          5                                                 323    12.5       5          5                                                 324    12.5       4          4                                                 326    12.5       5          5                                                 328    12.5       5          5      good                                       333    12.5       5          5      good                                       346    12.5       5          4                                                 347    12.5       4          4                                                 348    12.5       3          4                                                 349    12.5       4          5                                                 351    12.5       5          4      good                                       352    12.5       5          4      good                                       353    12.5       5          4      good                                       364    12.5       5          5      good                                       367    12.5       5          5      good                                       368    12.5       5          5      good                                       370    12.5       5          5      good                                       371    12.5       5          5      good                                       372    12.5       5          5      good                                       373    12.5       5          5      good                                       374    12.5       5          5      good                                       375    12.5       5          5      good                                       376    12.5       5          5      good                                       377    12.5       5          5      good                                       378    12.5       5          5                                                 379    12.5       5          5      good                                       381    12.5       5          5      good                                       383    12.5       5          5      good                                       386    12.5       5          5      good                                       389    12.5       5          5      good                                       391    12.5       5          5                                                 392    12.5       5          5      good                                       393    12.5       5          5      good                                       395    12.5       5          5      good                                       396    12.5       5          5      good                                       399    12.5       4          5                                                 400    12.5       5          5                                                 401    12.5       5          5      good                                       402    12.5       5          5      good                                       403    12.5       5          5      good                                       404    12.5       5          5      good                                       405    12.5       5          5      good                                       406    12.5       5          5      good                                       407    12.5       5          5      good                                       408    12.5       5          5      good                                       409    12.5       5          5                                                 410    12.5       5          5                                                 413    12.5       5          5      good                                       414    12.5       5          5      good                                       415    12.5       5          5      good                                       429    12.5       5                                                            430    12.5       5                                                            442    12.5       5          5      good                                       445    12.5       5          5      good                                       447    12.5       5          5      good                                       451    12.5       5          5      good                                       453    12.5       5          5      good                                       454    12.5       5          5      good                                       455    12.5       5          5      good                                       456    12.5       5          5      good                                       457    12.5       5          5      good                                       458    12.5       5          5      good                                       459    12.5       5          5      good                                       508    12.5       5          5                                                 694    12.5       5                                                            861    12.5       4                                                            868    12.5       4                                                            937    12.5       4                                                            Reference:                                                                     1 #STR13##                                                                     12.5          5          1                                                     ______________________________________                                    

Industrial Applicability

The compounds of the present invention have excellent fungicidal effectiveness, and therefore, are useful as a fungicide for agricultural and horticultural use. 

What is claimed is:
 1. Benzamidoxime derivatives represented by the formula I!: ##STR14## wherein R¹ is unsubstituted or substituted C₁ -C₄ alkyl, unsubstituted or substituted C₂ -C₄ alkenyl or unsubstituted or substituted C₂ -C₄ alkynyl,R² is heterocycle optionally having substituents, X¹ is C₁ -C₄ haloalkyl, X², X³, X⁴ and X⁵ are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkoxy, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl, nitro, amino or C₁ -C₄ alkylcarbonylamino, and r₁ and r₂ are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio or amino, or r₁ and r₂ may form carbonyl in together.
 2. Benzamidoxime derivatives represented by the formula I!: ##STR15## wherein R¹ is straight-chain or branched C₁ -C₄ alkyl; a group represented by a general formula, R³ CH₂, wherein R³ is a group selected from a group consisting of C₃ -C₈ cycloalkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy C₁ -C₃ alkylthio, C₁ -C₃ alkylsulfinyl C₁ -C₃ alkylsulfonyl, C₁ -C₃ alkoxycarbonyl, cyano, amino, C₁ -C₃ monoalkylamino, C₁ -C₃ dialkylamimo, acylamino and cyano; C₂ -C₄ alkenyl or C₂ -C₄ alkynyl,R² is 5- or 6-membered aromatic heterocycle containing 1 to 4 heteroatoms of one or more species selected from a group consisting of nitrogen, oxygen and sulphur, those which are optionally having one or more substituents selected from a group consisting of halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkyl and C₁ -C₃ haloalkoxy, X¹ is C₁ -C₄ haloalkyl, X², X³, X⁴ and X⁵ are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl, nitro, amino or C₁ -C₄ alkylcarbonylamino, and r₁ and r₂ are each independently hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio or amino, or r₁ and r₂ may form carbonyl in together.
 3. A fungicide for agricultural and horticultural use, comprising one or more of the benzamidoxime derivatives represented by the formula (I) in claim 1 wherein R¹, X¹, X², X³, X⁴, X⁵, R², r₁ and r₂ are as defined in claim 1 as the active principle and a carrier. 